3-BocNH-ABNO-catalyzed aerobic oxidation of alcohol at room temperature and atmospheric pressure

Tetrahedron Letters 60 (2019) 150994

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3-BocNH-ABNO-catalyzed aerobic oxidation of alcohol at room temperature and atmospheric pressure Yajing Zhao, Yutong Li, Zhenlu Shen ⇑, Xinquan Hu, Baoxiang Hu, Liqun Jin, Nan Sun, Meichao Li ⇑ College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China

a r t i c l e

i n f o

Article history: Received 10 June 2019 Revised 23 July 2019 Accepted 27 July 2019 Available online 30 July 2019 Keywords: Oxidation Molecular oxygen Alcohols Nitroxyl radicals

a b s t r a c t A transition-metal-free catalytic system has been developed for selective transformation of alcohol to aldehydes or ketones. The reactions were performed with 3-(tert-butoxycarbonylamino)-9-azabicyclo [3.3.1]nonane N-oxyl (3-BocNH-ABNO) as the catalyst, NaNO2 as the co-catalyst, molecular oxygen as the terminal oxidant, and AcOH as the solvent under room temperature. This catalytic system exhibited broad functional group tolerance. A series of alcohol substrates, including primary and secondary benzylic alcohols, heteroaromatic analogues, primary and secondary aliphatic alcohols, could be converted into their corresponding aldehydes and ketones in good conversions and selectivities. Ó 2019 Elsevier Ltd. All rights reserved.

Selective oxidation of alcohols to aldehydes or ketones is one of the most important organic chemical reactions. This reaction is widely used in fine chemical industry, pharmaceutical synthesis, flavor and fragrance industries [1]. To achieve this simple transformation, so far, a number of methods have been developed. Traditionally, alcohol oxidation were achieved by using stoichiometric oxidants, such as manganese oxides, chromium salts and the Dess-Martin reagent, which generated large amounts of inorganic and organic wastes [2]. In recent years, molecular oxygen has attracted more and more attention because of its abundant sources, low price and cleanliness [3]. From the viewpoint of economy and environmental protection, it is undoubtedly the best alternative to use molecular oxygen as the terminal oxidant in oxidation reaction. Based on these reasons, it needs great efforts to develop aerobic oxidation methods. In recent decades, use of 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO) or its derivatives as the catalyst in the aerobic oxidation of alcohols into carbonyl compounds has been widely reported [4]. As is known to all, the nitroxyl radical of TEMPO is surrounded by four methyl groups, which makes it possible to oxidize primary alcohols preferentially in the presence of secondary alcohols [5]. But this is precisely its disadvantage in the oxidation of sterically hindered primary and secondary alcohols. Thus use of less hindered nitroxyl radicals as the catalyst offer a method to resolve this issue (Scheme 1). For example, 2-azaadamantane N-oxyl (AZADO) was firstly synthesized by Dupeyre and Rassat in 1975, but only in recent years it ⇑ Corresponding authors. E-mail addresses: [email protected] (Z. Shen), [email protected] (M. Li). https://doi.org/10.1016/j.tetlet.2019.150994 0040-4039/Ó 2019 Elsevier Ltd. All rights reserved.

has been applied to alcohol oxidation [6]. Up to now, a lot of catalytic systems for alcohol oxidation in which AZADO or its derivatives were chosen as the catalyst together with all sorts of terminal oxidants such as hypochlorite, chlorite, azodicarboxylates and oxygen, have been established [7]. AZADO and its derivatives exhibited extraordinarily high catalytic activity compared with TEMPO and its derivatives. However there are some drawbacks in the procedure for the synthesis of AZADO and related nitroxyl derivatives, such as many synthetic steps and poor yields. In contrast, the synthetic procedures of 9-azabicyclo[3,3,1]nonane N-oxyl (ABNO) and its derivatives are relatively simple [8]. Recently, ABNO and ketoABNO have been widely employed as potent nitroxyl radicals for the oxidation of alcohols and other oxidation reactions [9], and they exhibited highly active nature compared with TEMPO. Previously, we reported a transition-metal-free catalytic oxidation system, TEMPO/tert-butyl nitrite (TBN)/O2, for the aerobic oxidation of alcohols. In this oxidation system, TEMPO was employed as the main catalyst, oxygen as the terminal oxidant, and TBN as the co-catalyst which served as an equivalent of nitric oxide [10]. This aerobic oxidation system was expanded from our previous oxidation systems, such as TEMPO/Br2/NaNO2/O2 [11], TEMPO/1,3-dibromo-5,5-dimethylhydantoin/NaNO2/O2 [12], TEMPO/HBr/TBN/O2 [13], and extended to the DDQ/TBN/O2 and TEMPO/DDQ/TBN/O2 oxidation systems [14]. In 2013, Stahl et al. successfully applied ABNO/NaNO2/AcOH/O2, ABNO/NaNO2/HNO3/ O2 and keto-ABNO/NaNO2/HNO3/O2 systems to the oxidation of alcohols [15]. Very recently, we developed ABNO/TBN/KPF6/O2 system for the oxidation of secondary alcohols in water [16]. To obtain a green, mild and efficient catalytic oxidation system, on the basis of literature and previous research work of our group,

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Y. Zhao et al. / Tetrahedron Letters 60 (2019) 150994

Scheme 1. Structures of different types of nitroxyl radicals.

herein we report a transition-metal-free catalytic system consisting of 3-(tert-butoxycarbonylamino)-9-azabicyclo[3.3.1]nonane N-oxyl (3-BocNH-ABNO), NaNO2 and AcOH for the selective aerobic oxidation of alcohols into their corresponding carbonyl compounds (Scheme 2). Though 3-BocNH-ABNO has been reported several years ago [17], to our knowledge, this work is the first example to apply 3-BocNH-ABNO to catalytic oxidation of alcohols with molecular oxygen as the terminal oxidant. The synthetic route toward 3-BocNH-ABNO is shown in Scheme 3 [15,17]. Benzylamine hydrochloride, glutaraldehyde and acetonedicarboxylic acid were used as the starting materials to synthesize the ketone 1. Then ketone 1 was converted into the oxime 2 in high yield. After reducing with NiCl2/NaBH4, the amine 3 was obtained in 75% yield. With the amine 3 in hand, subsequent N-Boc protection and removal of the benzyl group furnished the compound 5, which could be successfully oxidized into 3-BocNHABNO in the presence of Na2WO4
H2O and urea hydrogen peroxide. To explore a robust and reliable condition for the oxidation of alcohols into carbonyl compounds, benzyl alcohol was chosen as the model substrate (Table 1). The initial reaction of transformation benzyl alcohol to benzaldehyde was carried out with 10 mol % of NaNO2 in acetic acid under an oxygen balloon at 25 °C with 0.5 h. As we expected, the reaction would not take place in the absence of nitroxyl radical (Table 1, entry 1). Next, several nitroxyl radicals (3 mol%) were added to evaluate their ability to promote aerobic alcohol oxidation (Table 1, entries 2–8). When TEMPO, 4OH-TEMPO and 4-AcNH-TEMPO were used as the catalysts, the conversion of benzyl alcohol was less than 5% (Table 1, entries 2–4). The conversion of benzyl alcohol was dramatically increased to 47% in the presence of ABNO (Table 1, entry 5). Replacing ABNO with keto-ABNO, the conversion of benzyl alcohol was further increased to 60% (Table 1, entry 6). Unfortunately, 3-AcNH-ABNO almost did not work in this reaction (Table 1, entry 7). To our delight, when 3-BocNH-ABNO was added to the oxidation system, benzyl alcohol was smoothly converted to benzaldehyde in full conversion without other by-product (Table 1, entry 8). These rudimentary results indicated that 3-BocNH-ABNO/ NaNO2/AcOH system for aerobic oxidation of alcohols into carbonyl compounds was feasible and encouraged us to further

Scheme 2. Transformation of alcohols to carbonyl compounds.

explore the optimal reaction conditions. When the amount of was NaNO2 reduced to 8 and 5 mol%, the conversion of benzyl alcohol went down to 86 and 49%, respectively (Table 1, entries 9 and 10). However, the conversion of benzyl alcohol could be elevated to higher that 99% with 8 mol% of NaNO2 when the reaction time was prolonged to 0.7 h (Table 1, entry 12). Without NaNO2, the reaction was completely inhibited (Table 1, entry 11). Later on, the amount of 3-BocNH-ABNO was further examined. It was found that reducing the amount of 3-BocNH-ABNO was unfavorable to the reaction (Table 1, entries 13 and 14). Thus we finally concluded that 8 mol% of NaNO2, 3 mol% of 3-BocNH-ABNO in acetic acid under atmospheric pressure of O2 at room temperature in 0.7 h were appropriate for the complete transformation of benzyl alcohol to benzaldehyde. On the basis of these results, we explored the substrate scope and applied 3-BocNH-ABNO/NaNO2/AcOH system to a number of primary benzylic alcohols and their heteroaromatic analogs. We find that good catalytic reactivity could be achieved for tested alcohols with high efficiency and excellent functional group compatibility under mild conditions. As can be seen from Table 2, all kinds of primary benzylic alcohols could be completely transformed to their corresponding aldehydes within an hour in excellent selectivities and yields (Table 2, entries 1–11). The complete conversion of p-methylbenzyl alcohol to p-methyl benzaldehyde could be achieved in 0.8 h, while it would take 1 h for o-methylbenzyl alcohol and m-methylbenzyl alcohol to be fully converted into o-methyl benzaldehyde and m-methyl benzaldehyde (Table 2, entries 2–4). The oxidation of benzylic alcohols with electronwithdrawing groups, such as (4-chlorophenyl)methanol, (4-bromophenyl)methanol and (4-fluorophenyl)methanol, furnished the expected products with excellent yields in 0.8–1 h (Table 2, entries 5–7). In our previous TEMPO/TBN/O2 oxidation system, much longer reaction time for oxidation of p-nitrobenzyl alcohol was needed than that of other substrates [10a]. However it could be completely converted into p-nitrobenzaldehyde in 0.7 h under this ABNO/NaNO2/AcOH/O2 system (Table 2, entry 8). When p-trifluoromethylbenzyl alcohol was submitted to the reaction, 86% isolated yield of p-(trifluoromethyl)benzaldehyde could be obtained in 0.9 h (Table 2, entry 9). p-Methoxybenzyl alcohol and p-methylthiobenzyl alcohol were transformed smoothly, and afforded their corresponding aldehydes in 91–93% isolated yields (Table 2, entries 10 and 11). 2-Naphthaldehyde could be achieved in 94% isolated yield when naphthalen-2-ylmethanol was used as the substrate (Table 2, entry 12). When two heteroaromatic benzylic alcohols, pyridin-3ylmethanol and thiophen-2-ylmethanol were subjected to the reactions, the isolated yields of nicotinaldehyde and thiophene-2carbaldehyde could reach up to 84% and 90%, respectively (Table 2, entries 13 and 14). 5-Hydroxymethylfurfural is a key biomassbased platform chemical, which can be produced from biomassderived glucose, fructose, and cellulose [18]. As one of the most important derivatives of 5-hydroxymethylfurfural, 2,5-diformylfuran has various applications in industry [19]. A full conversion with 99% selectivity and 95% isolated yield of 2,5-diformylfuran could be obtained in 1 h when higher loading of catalysts (5 mol% of

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Y. Zhao et al. / Tetrahedron Letters 60 (2019) 150994

Scheme 3. Synthetic route toward 3-BocNH-ABNO.

Table 1 Optimization of the reaction conditions for benzyl alcohol oxidation.a

a b

Entry

Nitroxyl radical

Cat. (mol%)

NaNO2 (mol%)

Time (h)

Conv.b (%)

Select.b (%)

1 2 3 4 5 6 7 8 9 10 11 12 13 14

– TEMPO 4-OH-TEMPO 4-AcNH-TEMPO ABNO Keto-ABNO 3-AcNH-ABNO 3-BocNH-ABNO 3-BocNH-ABNO 3-BocNH-ABNO 3-BocNH-ABNO 3-BocNH-ABNO 3-BocNH-ABNO 3-BocNH-ABNO

– 3 3 3 3 3 3 3 3 3 3 3 2 1

10 10 10 10 10 10 10 10 8 5 – 8 8 8

0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.7 0.7 0.7

0 5 3 3 47 60 1 >99 86 49 0 >99 60 43

– >99 >99 >99 >99 >99 >99 >99 >99 >99 – >99 >99 >99

Reaction conditions: benzyl alcohol (1.0 mmol), AcOH (1 mL), 25 °C, O2 balloon. Determined by GC with area normalization method.

3-BocNH-ABNO and 10 mol% of NaNO2) were used (Table 2, entry 15). Having successfully achieved the aerobic oxidation of various primary benzylic alcohols, we next tried the 3-BocNH-ABNO/ NaNO2/AcOH catalytic system for transformation of secondary benzylic alcohols and aliphatic alcohols to their corresponding carbonyl compounds (Table 2, entries 16–29). Secondary benzylic alcohols and aliphatic alcohols displayed relatively low reactivity in the process of oxidation compared with primary benzylic alcohols. To settle this issue, the loading of catalysts were adjusted. Under modified conditions, several aromatic ketones and aliphatic aldehydes or ketones were smoothly obtained. When the loading of 3-BocNH-ABNO was increased to 5 mol%, the conversion of 1,2,3,4-tetrahydronaphthalen-1-ol was as high as 99% within 1.0 h, and the isolated yield of 3,4-dihydronaphthalen-1(2H)-one

was 98% (Table 2, entry 16). Benzophenone could be gained in 84% isolated yield when diphenylmethanol was selected as the substrate with 5 mol % of 3-BocNH-ABNO and 10 mol % of NaNO2 (Table 2, entry 17). To our delight, under the same oxidative conditions as diphenylmethanol, 1-phenylprop-2-yn-1-ol gave the desired ketone in 96% isolated yield (Table 2, entry 19), and 2phenylpropanal could be obtained in 93% isolated yield from 2phenylpropan-1-ol after a reaction time of 1.5 h (Table 2, entry 23). Some nitroxyl radical-based oxidation systems have problem to deal with the substrates bearing an alpha-chirality [1c]. Thus (R)-2-phenylpropan-1-ol was submitted to this aerobic oxidation system, it was found that (R)-2-phenylpropanal could be achieved without epimerization (Table 2, entry 24). For some substrates that were more difficult to be oxidized, the amount of 3-BocNH-ABNO and NaNO2 should be increased to 8 mol% and

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Y. Zhao et al. / Tetrahedron Letters 60 (2019) 150994

Table 2 Aerobic oxidation of alcohols into carbonyl compounds.a

Time (h)

Conv.b (%)

Select.b (%)

Yield (%)

1

0.7

>99

>99

(99)

2

0.8

>99

>99

90

3

1.0

>99

>99

91

4

1.0

>99

>99

86

5

0.9

>99

>99

98

6

1.0

>99

>99

95

7

0.8

>99

>99

(99)

8

0.7

>99

>99

98

9

0.9

>99

>99

86

10

0.8

>99

>99

93

11

1.0

>99

>99

91

12

0.9

>99

>99

94

13

0.8

>99

>99

84

14

0.9

>99

>99

90

15d

1.0

>99

>99

95

16e

1.0

>99

>99

98

17d

1.0

91

>99

84

Entry

Substrates(a)

Products(b)

c

5

Y. Zhao et al. / Tetrahedron Letters 60 (2019) 150994 Table 2 (continued) Time (h)

Conv.b (%)

Select.b (%)

Yield (%)

18f

1.5

98

>99

92

19d

1.5

>99

>99

96

20f

1.5

91

>99

81

21f

1.0

87

>99

83

22f

1.5

90

>99

(90)

23d

1.5

95

>99

93

24d

1.5

95

>99

92

25f

1.5

>99

>99

82

26f

1.5

91

>99

(91)

27f

1.5

90

>99

(90)

28f

4.0

88

>99

(88)

29f

2.0

95

>99

91

Entry

a b c d e f

Substrates(a)

Products(b)

c

Reaction conditions: 1 (1 mmol%), 3-BocNH-ABNO (3 mol%), NaNO2 (8 mol%), AcOH (1 mL), 25 °C, O2 balloon. Determined by GC with area normalization method. Conv.: conversion of substrate; Select.: selectivity between product and side products. Isolated yield, values in parentheses were determined by GC with area normalization method. 3-BocNH-ABNO (5 mol%), NaNO2 (10 mol%). 3-BocNH-ABNO (5 mol%). 3-BocNH-ABNO (8 mol%), NaNO2 (10 mol%).

10 mol%, respectively. 1-(Naphthalen-2-yl)ethanone could be obtained from 1-(naphthalen-2-yl)ethanol in 92% isolated yield in 1.5 h (Table 2, entry 18). 1-(4-Fluorophenyl)ethanone and 1(4-cyanophenyl)ethanone could be achieve from 1-(4fluorophenyl)ethanol and 4-(1-hydroxyethyl)benzonitrile with isolated yields above 80% (Table 2, entries 20 and 21). In addition, undec-10-en-1-ol, octan-2-ol, cycloheptanol and pent1-yn-3-ol could be converted into undec-10-enal, octan-2-one, cycloheptanone and pent-1-yn-3-one in excellent selectivities (Table 2, entries 22 and 25–27). Adamantan-2-ol was difficult to be transformed to adamantan-2-one. When the reaction time

was prolonged to 4 h, 88% GC yield of adamantan-2-one could be achieved (Table 2, entry 28). Moreover, 95% conversion of isoborneol could be achieved within 1.0 h, and the desired product could be isolated in 91% yield (Table 2, entry 29). Based on the previous literatures [9a,9e,16], a plausible reaction mechanism for the transformation of alcohol into corresponding carbonyl compound was proposed (Scheme 4). Under acidic condition NO can be released form NaNO2, and it will be easily converted into NO2 in the presence of O2. Then 3-BocNH-ABNO is oxidized to 3-BocNH-ABNO＋ by NO2. 3-BocNH-ABNO＋ possesses strong oxidation ability, which can oxidize the alcohol to its

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Y. Zhao et al. / Tetrahedron Letters 60 (2019) 150994

Scheme 4. A proposed overall reaction mechanism.

corresponding aldehyde or ketone. At the same time 3-BocNHABNO+ is reduced to 3-BocNH-ABNOH. 3-BocNH-ABNOH can be re-oxidized to 3-BocNH-ABNO＋ by NO2. In summary, we have successfully applied a transition-metalfree catalytic oxidation system, 3-BocNH-ABNO/NaNO2/AcOH/O2, for the oxidation of alcohols at room temperature. This green catalytic oxidation system displayed high reaction efficiency, especially for primary benzylic alcohols. A broad range of alcohol substrates, including primary and secondary benzylic alcohols, heteroaromatic analogues, primary and secondary aliphatic alcohols, could be converted into their corresponding aldehydes and ketones in good conversions and selectivities, with excellent functional group tolerance. This catalytic oxidation system is environmentally benign and provides an efficient method to prepare various aldehydes and ketones from alcohols. Acknowledgements This work was financially supported by the National Natural Science Foundation of China (21773211, 21776260 and 21773210) and Natural Science Foundation of Zhejiang Province (LY17B060007). Appendix A. Supplementary data Supplementary data to this article can be found online at https://doi.org/10.1016/j.tetlet.2019.150994. References [1] (a) V. Satam, A. Harad, R. Rajule, H. Pati, Tetrahedron 66 (2010) 7659; (b) S. Dash, S. Patel, B. Mishra, Tetrahedron 65 (2009) 707; (c) L. Yang, Z. Lin, S. Shao, Q. Zhao, R. Hong, Angew. Chem. Int. Ed. 57 (2018) 16200; (d) B.L. Ryland, S.S. Stahl, Angew. Chem. Int. Ed. 53 (2014) 8824. [2] (a) J. March, Advanced Organic Chemistry: Reactions Mechanisms and Structure, 4th ed., John Wiley & Sons, New York, 1992; (b) G. Tojo, M. Fernández, Oxidation of Alcohols to Aldehydes and Ketones, Springer, New York, 2010; (c) G. Tojo, M. Fernández, Oxidation of Primary Alcohols to Carboxylic Acids, Springer, New York, 2010. [3] (a) R.A. Sheldon, I.W.C.E. Arends, G.J.T. Brink, A. Dijksman, Acc. Chem. Res. 35 (2002) 774; (b) B.Z. Zhan, A. Thompson, Tetrahedron 60 (2004) 2917; (c) S.S. Stahl, Angew Chem. Int. Ed. 43 (2004) 3400; (d) I.E. Markó, P.R. Giles, M. Tsukazaki, I. Chellé-Regnaut, A. Gautier, R. Dumeunier, F. Philippart, K. Doda, J. Mutonkole, S.M. Brown, C.J. Urch, Adv. Inorg. Chem. 56 (2004) 211; (e) C. Parmeggiani, F. Cardona, Green Chem. 14 (2012) 547; (f) I.P. Skibida, A.M. Sakharov, Catal. Today 27 (1996) 187; (g) Y.-K. Hu, L. Chen, B.-D. Li, Catal. Commun. 103 (2018) 42; (h) R. Ray, S. Chandra, D. Maiti, G.K. Lahiri, Chem. Eur. J. 22 (2016) 8814; (i) M.A. Nasseri, K. Hemmat, A. Allahresani, E.H. Hajiabadi, Appl. Organometal. Chem. 33 (2019) 4809; (j) Z.-Z. Shi, C. Zhang, C.-H. Tanga, N. Jiao, Chem. Soc. Rev. 41 (2012) 3381.

[4] (a) N.W. Wang, R.H. Liu, J.P. Chen, X.M. Liang, Chem. Commun. 37 (2005) 5322; (b) X.L. Wang, X.M. Liang, Chin. J. Catal. 29 (2008) 935; (c) L. Lin, L.Y. Ji, Y.Y. Wei, Catal. Commun. 9 (2008) 1379; (d) S.M. Ma, J.X. Liu, S.H. Li, B. Chen, J.J. Cheng, J.Q. Kuang, Y. Liu, B.Q. Qiang, Y.L. Wang, J.T. Ye, Q. Yu, W.M. Yuan, S.C. Yu, Adv. Synth. Catal. 353 (2011) 1005; (e) T. Dohi, K. Fukushima, T. Kamitanaka, K. Morimoto, N. Takenagab, Y. Kita, Green Chem. 14 (2012) 1493; (f) J.M. Hoover, B.L. Ryland, S.S. Stahl, J. Am. Chem. Soc. 135 (2013) 2357; (g) B.L. Ryland, S.D. McCann, T.C. Brunold, S.S. Shannon, J. Am. Chem. Soc. 136 (2014) 12166; (h) K. Lagerblom, J. Keskiväli, A. Parviainen, J. Mannisto, T. Repo, ChemCatchem 10 (2018) 2908; (i) X.-G. Jiang, J.-X. Liu, S.-M. Ma, Org. Process Res. Dev. 23 (2019) 825; (j) L. Marais, A.J. Swarts, Catalysts 9 (2019) 395; (k) J.M. Hoover, J.E. Steves, S.S. Stahl, Nat. Protoc. 7 (2012) 1161; (l) J.M. Hoover, S.S. Stahl, J. Am. Chem. Soc. 133 (2011) 16901; (m) T. Hirashita, M. Nakanishi, T. Uchida, M. Yamamoto, S. Araki, I.W.C.E. Arends, R.A. Sheldon, ChemCatChem 8 (2016) 2704; (n) K. Lagerblom, P. Wrigstedt, J. Keskiväli, A. Parviainen, T. Repo, ChemPlusChem 81 (2016) 1160; (o) W.-H. Liu, J.-H. Yang, J. Cai, Res. Chem. Intermediat. 45 (2019) 549; (p) T. Chen, Z.-K. Xu, L. Zhou, L.-Y. Hua, S. Zhang, J.-P. Wang, Tetrahedron Lett. 60 (2019) 419; (q) A.J. Shakir, C. Paraschivescu, M. Matache, M. Tudose, A. Mischie, F. Spafiu, P. Ionita, Tetrahedron Lett. 56 (2015) 6878. [5] A.E.J. Denooy, A.C. Besemer, H. Vanbekkum, Synthesis 10 (1996) 1153. [6] (a) Y. Demizu, H. Shiigi, T. Oda, Y. Matsumura, O. Onomura, Tetrahedron Lett. 49 (2008) 48; (b) C.J. Zhu, Z. Zhang, W.W. Ding, J.J. Xie, Y. Chen, J.L. Wu, X.C. Chen, H.J. Ying, Green Chem. 16 (2014) 1131. [7] (a) M. Shibuya, M. Tomizawa, I. Suzuki, Y. Iwabuchi, J. Am. Chem. Soc. 128 (2006) 8412; (b) M. Tomizawa, M. Shibuya, Y. Iwabuchi, Org. Lett. 11 (2009) 1829; (c) M. Hayashi, Y. Sasano, S. Nagasawa, M. Shibuya, Y. Iwabuchi, Chem. Pharm. Bull. 43 (2011) 1570; (d) M. Shibuya, Y. Osada, Y. Sasano, M. Tomizawa, Y. Iwabuchi, J. Am. Chem. Soc. 133 (2011) 6497; (e) M. Hayashi, M. Shibuya, Y. Iwabuchi, J. Org. Chem. 77 (2012) 3005; (f) M. Shibuya, S. Nagasawa, Y. Osada, Y. Iwabuchi, J. Org. Chem. 79 (2014) 10256; (g) Y. Sasano, N. Kogure, T. Nishiyama, S. Nagasawa, Y. Iwabuchi, Chem. Asian J. 10 (2015) 1004; (h) R. Doi, M. Shibuya, T. Murayama, Y. Yamamoto, Y. Iwabuchi, J. Org. Chem. 80 (2015) 401; (i) N. Fukuda, M. Izumi, T. Ikemoto, Tetrahedron Lett. 56 (2015) 3905; (j) M. Shibuya, K. Furukawa, Y. Yamamoto, Synlett 28 (2017) 1554; (k) C.-J. Zhu, Z. Zhang, W.-W. Ding, J.-J. Xie, Y. Chen, J.-L. Wu, X.-C. Chen, H.-J. Ying, Green Chem. 16 (2014) 1131. [8] M. Shibuya, M. Tomizawa, Y. Sasano, Y. Iwabuchi, J. Org. Chem. 74 (2009) 4619. [9] (a) B. Karimi, E. Farhangi, H. Vali, S. Vahdati, ChemSusChem 7 (2014) 2735; (b) L. Rogan, N.L. Hughes, Q. Cao, L.M. Dornan, M.J. Muldoon, Catal. Sci. Technol. 4 (2014) 1720; (c) G.Q. Zhang, C.X. Yang, E. Liu, L. Li, J.A. Golen, A.L. Rheingold, RSC Adv. 4 (2014) 61907; (d) J.E. Steves, S.S. Stahl, J. Org. Chem. 80 (2015) 11184; (e) Y. Kadoh, M. Tashiro, K. Oisaki, M. Kanai, Adv. Synth. Catal. 357 (2015) 2193; (f) J.Q. Ma, Y. Wan, C. Hong, M.C. Li, X.Q. Hu, W.M. Mo, B.X. Hu, N. Sun, L.Q. Jin, Z.L. Shen, Eur. J. Org. Chem. (2017) 3335; (g) Y. Wan, J.-Q. Ma, C. Hong, M.-C. Li, L.-Q. Jin, X.-Q. Hu, B.-X. Hu, W.-M. Mo, N. Sun, Z.-L. Shen, Chin. Chem. Lett. 29 (2018) 1269; (h) J.E. Steves, Y. Preger, J.R. Martinelli, C.J. Welch, T.W. Root, J.M. Hawkins, S.S. Stahl, Org. Process Res. Dev. 47 (2015) 1548; (i) L.Y. Wang, S.S. Shang, G.S. Li, L.H. Ren, Y. Lv, S. Gao, J. Org. Chem. 81 (2016) 2189; (j) M.J. Kim, Y.E. Jung, C.Y. Lee, J. Kim, Tetrahedron Lett. 59 (2018) 2722; (k) M.J. Kim, J. Kim, Bull. Korean Chem. Soc. 39 (2018) 711; (l) J. Kim, S.S. Stahl, ACS Catal. 3 (2013) 1652; (m) S.L. Zultanski, J.Y. Zhao, S.S. Stahl, J. Am. Chem. Soc. 138 (2016) 6416; (n) A.J.J. Lennox, S.L. Goes, M.P. Webster, H.F. Koolman, S.W. Djuric, S.S. Stahl, J. Am. Chem. Soc. 140 (2018) 11227; (o) K.C. Miles, M.L. Abrams, C.R. Landis, S.S. Stahl, Org. Lett. 18 (2016) 3590. [10] (a) X.J. He, Z.L. Shen, W.M. Mo, N. Sun, B.X. Hu, X.Q. Hu, Adv. Synth. Catal. 351 (2009) 89; (b) C.J. Fang, M.C. Li, X.Q. Hu, W.M. Mo, B.X. Hu, N. Sun, L.Q. Jin, Z.L. Shen, Adv. Synth. Catal. 358 (2016) 1157. [11] R.H. Liu, X.M. Liang, C.Y. Dong, X.Q. Hu, J. Am. Chem. Soc. 126 (2004) 4112. [12] R.H. Liu, C.Y. Dong, X.M. Liang, X.J. Wang, X.Q. Hu, J. Org. Chem. 70 (2005) 729. [13] Y. Xie, W.M. Mo, D. Xu, Z.L. Shen, N. Sun, B.X. Hu, X.Q. Hu, J. Org. Chem. 72 (2007) 4288. [14] (a) Z.L. Shen, M. Chen, T.T. Fang, M.C. Li, W.M. Mo, B.X. Hu, N. Sun, X.Q. Hu, Tetrahedron Lett. 56 (2015) 2768; (b) C.B. Qiu, L.Q. Jin, Z.L. Huang, Z.Q. Tang, A.W. Lei, Z.L. Shen, N. Sun, W.M. Mo, B.X. Hu, X.Q. Hu, ChemCatChem 4 (2012) 76;

Y. Zhao et al. / Tetrahedron Letters 60 (2019) 150994

[15] [16] [17] [18]

(c) Z.L. Shen, J.L. Dai, J. Xiong, X.J. He, W.M. Mo, B.X. Hu, N. Sun, X.Q. Hu, Adv. Synth. Catal. 353 (2011) 3031; (d) J.Q. Ma, Z.M. Hu, M.C. Li, W.J. Zhao, X.Q. Hu, W.M. Mo, B.X. Hu, N. Sun, Z.L. Shen, Tetrahedron 71 (2015) 6733. M.B. Lauber, S.S. Stahl, ACS Catal. 3 (2013) 2612. J.Q. Ma, C. Hong, Y. Wan, M.C. Li, X.Q. Hu, W.M. Mo, B.X. Hu, N. Sun, L.Q. Jin, Z.L. Shen, Tetrahedron Lett. 58 (2017) 652. M.C. Frantz, E.M. Skoda, J.R. Sacher, M.W. Epperly, J.P. Goff, J.S. Greenberger, P. Wipf, Org. Biomol. Chem. 11 (2013) 4147. (a) J.J. Bozell, G.R. Petersen, Green Chem. 12 (2010) 539; (b) M.E. Zakrzewska, E. Bogel-Lukasik, R. Bogel-Lukasik, Chem. Rev. 111 (2011) 397; (c) J. Zhang, X.X. Yu, F.X. Zou, Y.H. Zhong, N. Du, X.R. Huang, ACS Sustain. Chem. Eng. 3 (2015) 3338; (d) J.X. Zhou, Z. Xia, T.Y. Huang, P.F. Yan, W.J. Xu, Z.W. Xu, J.J. Wang, Z.C. Zhang, Green Chem. 17 (2015) 4206; (e) J.Z. Chen, K.G. Li, L.M. Chen, R.L. Liu, X. Huang, D.Q. Ye, Green Chem. 16 (2014) 2490; (f) S. Siankevich, Z.F. Fei, R. Scopelliti, P.G. Jessop, J.G. Zhang, N. Yan, P.J. Dyson, ChemSusChem 9 (2016) 2089;

7

(g) C. Zhang, Z.T. Cheng, Z.H. Fu, Y.C. Liu, X.F. Xi, A.M. Zheng, S.R. Kirk, D.L. Yin, Cellulose 24 (2017) 95. [19] (a) J. Artz, S. Mallmann, R. Palkovits, ChemSusChem 8 (2015) 672; (b) K. Ghosh, R.A. Molla, M.A. Iqubal, S.S. Islam, S.M. Islam, Appl. Catal. A 520 (2016) 44; (c) M.O. Kornpanets, O.V. Kushch, Y.E. Litvinov, O.L. Pliekhov, K.V. Novikova, A. O. Novokhatko, A.N. Shendrik, A.V. Vasiyev, I.O. Opeida, Catal. Commun. 57 (2014) 60; (d) X.X. Liu, J.F. Xiao, H. Ding, W.Z. Zhong, Q. Xu, S.P. Su, D.L. Yin, Chem. Eng. J. 283 (2016) 1315; (e) R.Q. Fang, R. Luque, Y.W. Li, Green Chem. 18 (2016) 3152; (f) F.H. Xu, Z.H. Zhang, ChemCatChem 7 (2015) 1470; (g) M. Chatterjee, T. Ishizaka, A. Chatterjeeb, H. Kawanami, Green Chem. 19 (2017) 1315; (h) A. Rapeyko, K.S. Arias, M.J. Climent, A. Corma, S. Iborra, Catal. Sci. Technol. 7 (2017) 3008; (i) M. Ventura, F. Lobefaro, E. Giglio, M. Distaso, F. Nocito, A. Dibenedetto, ChemSusChem 11 (2018) 1305; (j) Z.-J. Wei, S.-W. Xiao, M.-T. Chen, M. Lu, Y.-X. Liu, New J. Chem. 43 (2019) 7600.