Hydroformylation catalysed by rhodium complexes of trehalose-derived ligands aa and ββ -tredip; a highly recioselective route to α-methylarylpropionaldehydes

Hydroformylation catalysed by rhodium complexes of trehalose-derived ligands aa and ββ -tredip; a highly recioselective route to α-methylarylpropionaldehydes

W404020186 S3.W+.Ul Q 19245 PngMlocl Jo& Ltd. Tefnzkdmn Vol. 42, No. 16, pp. 5105 to 5109,1986 Printed in GreatBrkain. HYDROFORMYLATION CATALYSEDBY ...

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W404020186 S3.W+.Ul Q 19245 PngMlocl Jo& Ltd.

Tefnzkdmn Vol. 42, No. 16, pp. 5105 to 5109,1986 Printed in GreatBrkain.

HYDROFORMYLATION CATALYSEDBY RHODIUMCOMPLEXES OF TREHALOSE-DERIVED A HIGHLYRECIOSELECTIVEROUTE LIGANDS-aa and gg-TREDIP; TOr-METiiYLARYLPROPIONALDEHYDES (Dyson Perrins

JOHNPi. BROWNand STEPHENJ. COOK Laboratory, South Parks Road, OXFORDOX1 3QY)

RIAZ KHAN Lyle Memorial Laboratory, Tate and Lyle Research, Reading) (Receiwd in UK 13 June 1986) Rhodium complexes of the ligand cc-TREDIP give 62:l lso-regioselectivity in Abstract: the hydroformylatlon of styrene under ambiex conditions wlthou=xcess phosphine. higher The results are compared with those obtained with than any previously reported value. other ligands. and extended to the preparation of 2-(6-methoxy-2-naphthylj-propanal. a precursor of the anti-inflammatory drug naproxen. (Philip

It has been known for hydroformylation terminal

aliphatic

aldehydes;

over

fifteen

of olefins olefins

the former

years

are converted

process

in organic

scope.

a general

This may reflect

and inhibitions of

substrate

against

sufficient

behind

trans.-chelation involves

working

flexibility (bite

stages

for

selectivity.

A chelating

Hydroformylatlon

precursor 1:l

alternative CO/H, (1:l was obtained Results 20 h.

formed

if

large

gas,

quantities

llgands

angle

with

90-120’)

and also

pathway in hydroformylation

, and with PPh, they may be mutually --cis or trans at increases

because

alleviate

with increasing

competitive

this

problem

ligation lf

phosphlne:

by CO lowers

cocomplexation

of

its

the donor

in situ.

and -BB-TREDIP. 1 and 2, with the cis chelating derived blphosphlne 4. Rather than prepare a number of

, a standard method was sought for conducting Crabtree

and Morris

have already

from the blcyclo~2,2,l~heptadlenerhodlum

this

latter

approach or 1:2)

complex may be prepared

was to react

obtained

(occasionally

the

in dichloromethane

and hydroformylation

up and analysed

has unusual

of styrene

method starting

’ since

the

molarity.

were carried

rhodium complexes

complex

base,

should

(bite

catalytic

The selectivity

monophosphines,

out with -MDIOP 3, and with the L-iditol

blphosphine

occasionally

of biphosphlne

to permit -cis-chelation

high effective

it

this,

to work with synthesis

, essential

pressure

Thus branched

are involved.

to rhodium

biphosphine

into Despite

although chemists

the

manner.’

and vinylarenes

rare’

than atmospheric

cycle.’

PPh, and other

atoms has a supficiently

is rather

catalyse

selective

significance.’

among organic

The major selective

coordinated

l

aldehydes

work has been the preparation

180’).

complexes

in a highly

commercial

synthesis

at higher

in the catalytic

rhodium ratio

Reactions

this

angle

linear

reluctance

in the backbone

two phosphines

different

into

and modest amounts of catalyst

The rationale

rhodium phosphine

conditions

is of considerable

usage of hydroformylatlon l

that

under very mild

by g.1.c.

in Table if

reaction

bisphosphlne

directly

hydroformylation the basis

cation

from (C,H,),Rh+

with an equivalent

in the presence

proceeded

are recorded up to 45 h.

ligand

provided

and an equivalent

and the phosphine.

of trls(allyl)rhodlum’

of substrate,

with a

OP one such of An

under

whereupon a deep red solution

smoothly. 1.

The reaction

was incomplete

mixture at that

was normally stage)

at 20’

stirred

for

and then worked

J. M. BROWNel al.

5106 TABLE 1

Hydroformylation

Run

Llgand

of styrene

Precursora

H&O

I Ndehydeab

Isa/n

1

2 PPh,

A

1:l

99.5

2

3

A

1:l

71

4.00

3

3

B

1:l

99

2.1c

1 43

5

4

A

1 :l

100

1 1.2

5

1

A

1 :l

70

9.4

6

1

A

2:l

90

4

17.5

7

1

B

1:l

8

1

B

2:l

9

2

A

1:l

10

2

A

2:l

11

2

B

1 :l

69

11.2

12

2

B

2:l

85

15.9

100

so’ 100

93 is0

n

-

a Precursor A IS trIa(allyl)rhodIum and precursor B is bla(bIcyalo[2,2,1]heptadlene)rhodIum In-eaohxe the precursor (0.018 -1) and tetrafluoroborate s two equivalents of NEt,. blphoaphine (0.018 ml) were dissolved in CH,Cl, (1 ml.) and degaaeed under argon. Styrene (0.44 mmol) wan added, argon replaced by CO/Hz and uptake of gas monitored by burette. The reaotlon mixture !a8 passed through a short column of silica gel and analyaed dlreatly by g.1.c :3% Carbouax, 120 1. Recovered starting material and reduced product were not distinguished in this analysis. C Single runs, otherwise experiments conducted at least In duplioate. The moat interesting

feature

of these

obeerved

with -oa TREDIP 1 and precursor literature. In WflkInaon’a early work, selectivity

of

8:l

in

gave aelectivitiea phosphine.’

Other cases Include

CHIRAPHOScomplexes,** ratio

of

towards groups ratio

12.9:1

for

both

the rate

that

to employ a substantial

high selectivity

of

observed

the reactivity

of

of the backbone

indioates

energy

barrier.

that This

case

oxygen-coordination

interoonversion

that

may remain bound to rhodium throughout

of affairs

the catalytic

styrenes

some special

may be -018 or The inherent should

for

cycle,

a

electron-withdrawing that

the ligand

Is possible.”

state

and

being E-NO, with an e:n

between the two geometries

is a very favourable

of isomer

catalyst,

of E-substituted

1 a suggests

of

up to lO:l,

of Wilklnaona

I* the beat.oaae

In the case

It has been shown that rhodium complexes and In the latter

giving

analogues

It was demonstrated

monophoaphlnea

exoeaa(>4:1)

of the branohed-chain

of dibenz.ophoaphole,*”

by HRh(PPh,),

In the

lao/n

work with chiral

In favour

polymer-supported

reported

HRhCO(PPh,), effected

Subsequent

and the regloaeleotIvIty,

trana-chelated.

high regioaeleotIvIty

than any case

of atyrene.’

In a comparison

catalyaed

The high selectivity

may be Involved.

the chelate

Yith

more selective

use necessary

derivatives

16:l.

was achieved.”

increased

intrinsic

which it

chelating

Is the reproducibly

being

was reported

where a reasonably

giving

hydroformylatlon

of 25:l.

it

the hydroformylatlon

up to 49:l

has been recorded

experiments

B, this

oocur

flexIbllIty with a low

hydroformylatlon

as Indicated

feature

since

in Figure

1.

The -66 Isomer 2 favours -cls-coordination w)re and trana-coordination rather less than does the wa-isomer 1, and it is notably leas affeotlve aa a regioaeleotive hydroformylation catalyst. The hydroformylatlon effort

haa been devoted

moderate.“’ 75%)‘.

PtCl,

purity

complexes

but the reaction

branched-chain of

vaniahingly

isomer

product small,

of atyrene

to P-phenylpropanal

to asymmetric

in the presence

of SnCl,

must be run at high pressure and over

was examined

hydrogenation, by N.m.r.

as might be expected

is

chiral for

introduces

a new chiral

With rhodium aomplexea’the

oatalyala.

give

a ligand

enantiomer

and the selectivity,

rather

shift

much better

weak.

analysis

centre,

results

and much

are uniformly

exoeaaes

both towards

(up to

the

In the present

case

using

and shown to be

Eu(hfc),

with a high degree

of baokbone

the optical flexIbIlIty.

Hydroformylationcalalyscdby rhodiumcomplexes

Figure 1 A hydroiormylatlon route to Naproxen 2-Arylproplonlc clinlcally

acids ere an Important clans of antIInfl.ammatory agente,l’

viable drugs Buren 5, Roben 6. Suproren 7 and Naproxen 8.

hydroiormylation by ao-lWDIP rhodium complexes wae examined by application enalcgue

.

cross-coupling

0r

eelective

to a Naproxen

Present routes to the oompound involve straightrorward aratlc

nickel-oatalyeed

Including the

The generality chemistry”

between 2-(bromomegneslo)-6wthoxynaphthalene

or

and the cssgne8Ium

salt oi ethyl P-bromoproplonate.”

&O””

yaw (qJOOH c”o$&oo”

5

6

O

Synthesis or 6-ethenyl-2-methoxynaphthalene brcvalde with 2-Iodo-6-wthoxynaphthalene

3

7

8

9 was eireoted by oross-aoupllng

In the presenoe oi a catalytic

vinylmagnesium

amount oi Pd(PPh,),*’

uhloh

gave the desired product in 691 yield.

Hydroiornylatlon wax.carried out according to procedure A,

end gave a mixture ol the two aldehydes

10 and 11 in

the oatalyst

Is optloally

active,

the reaction

ratio 20:1,

basis or Its ‘H N.m.r. spectrum In the presence or Eu(hic),. naproxen esters using the lipase

,,,p

3

9

10

11

0r

been reported.”

04” $x+0 3

Although

raoemic, judged on the

hzylPat.10 resolution

rrcm Candida oyllndracea has reoently

--”

3

In 94.51 Isolated yield.

product 10 is eiieotlvely

racemlo

J. M. BROWN er al.

5108 Two

further results

act-l-one,

should be reoorded. Firstly the seleotivlty in hydroformylation ot where n-nonanal predominates, is Lowry when o(r-TREDIPis employed in proaedure A. slnue

28% of the branched-chain Isomer was observed, compared with around 101 when PPh,-based catalysts are used.&

Purther the hydroformylatlon of phenyl vinyl sulphoxide gives 971 of the branched-ohaln

aldehyde 12 with E-TREDIP as catalyst.

One dlastereomer appears to predominate In the ‘H N.a.r.

spectrum of crude prodwt but this may refleot rather ,acIdic.

and faollltate

keto

thermodynamio control since the g-proton will

en01 Interoonverslon.

The reaction

is very slcu,

be

however,

and only a few turnovers were achieved in 48 h. under ambient conditions. Aoknowledgment We thank SERCfor a and Johnson-Matthey p.1.0.

CASE

studentship (to SJC In collaboration

with Tate and Lyle)

for the loan of rhodium salts.

Experlwntal Trls(allyl)rhodiumr’ tetrafluoroborate” and -bls(bIcyolo[2,2,1~heptadIene)rhodium tetrak18(tr1pheny1phoaph1ne)pa11ad1um1’ were prepared by published proaedurea. All reactions Involving organometalllc

complexes were conducted under an inert atmosphere using vaouumline

and Suhlenk techniques as previously desorlbed. 2-Iodo-6-methoxynaphthalene 2-Methyl-2-propylllthlum in pentane (1.4 M, 70 ml, 98 mm011was added to a solution of 2-braao-6-methoxynaphthalene*’ (10.01 g, 42.2 -1) in tetrahydrofuran (90 ml) at -78’. The mixture was stirred at -78’ for lh, a solution of Iodine (16.85 g, 66.4 mmol) In tetrahydrofuran (7Ou1l) was added, and the mixture was then stirred at room tslaperature for 72h. The solvent was re moved in vaouo, dlohloromethane (250 ml) was added and the solution was washed with water (100 ml-saturated sodium thiosulphate solution (4 x 100 ml), water (100 ml) and saturated sodium chloride solution (100 ml) and then dried (anhydrous magneslu sulphate). Ttm solvent was rwved in vacua and the residue recrystallized from dlchloromathane/methanol to give 2-lodod-osthoxym.p. 143-4@1 ‘H-N.m.r.r 6 (300 MHz. (10.03 gm. 35.3 llrmol, 83.7%) as yellow plates; (3H, a, One), 7.05-7.7 (5H, m, arom), 8.15 (lH, m, arm, ortho-H); found: C, 46.50; H, 3.28: C,,H,IO requires: C, 46.50; H, 3.191. 6-Ethenyl-2-methoxynaphthalene Tetrakis(trIphenylphosphIne)palladlum (0) (171) (0.100 g, 0.087 mwl) was added to a mixture of 2-iodo-6-methoxynaphthalene (0.99 g, 3.48 msorln tetrahydrofuran (15 ml) and vinylmagneslllm bromide (0.8 Fl, 12 ml, 9.6 mm011In tetrahydrofuran at -78’. The solution was stlrrod under argon at room temperature for 5d, during which time It beoame brown and a white precipitate was formed. Hydrochlorlo aold (3 M, 4 ml, 12 mm011was added, the solvent was removed in vacua, dlchloroplethane [!j; ml; and water (50 ml) were added, and the aqueous layer wss extraoted with dlohloromsthane . The combined organic layers were washed with saturated sodium hydrogen oarbonate solution (50 ml), water (2 x 50 ml) and saturated sodium chloride solution. The solution was dried (anhydrous ma$esIum 8ulphat.e) and the solvent removed In vacua to give an orange residue whloh was sublimed (100 1 as a white solid, examination of whloh by ‘H-NW showed a mixture of 6-ethenyl-2-methoxynaphthalene (881) and 2-methoxynaphthalene (121). Reorystalllzation from m.p. 92-3. ethanol/water gave pure 6-ethenyl-2-methoxynaph thalene (0.440 g, 2.39 mreol, 68.65); (lit.“@ 93-4*1: ‘H-NMr 6 (300 MHz, CDCl,) 3.95 (3H, 8, OrCe), 5.3 (1H. d, J 10.5 Hz. -C&,Hg). 5.85 (lH, d, J 17 Hz. -CH H 1, 6.85 (lH, dd, Jm 10.5 Hz, Jm 17 Hz, CaHg), 7.15 (2H, m, arod, 7.6-7.75 (4H, m, arom A-f. 2*(2-methoxy-6-naphthylFpropana1 6-Ethenyl-2-methoxynaphthalene (166) (100 mg. 0.543 -1) was added to a degassed aolutlon of the blphosphlne aa-TREDIP (28 mg, O.Ormmol) and trls(allyl)rhodlum (8 mg, 0.035 !maoi) in hydrogen/carbon monoxide (1:l ratio) for dichloromethane T? ml). The solution was stirred ar The solvent was 48h.. and then passed through a column of silica gel to remove the rhodium salts. removed In vacua and examination of the crude product (‘H-NW Indicated the presence of 21(2-met~aphthyl)-propanal (951) and 3-(6-methoxy-2-naphthyl-propanal (5%). There was no Subllmatlon of the product gave a white solid (110 mg, 0.513 -1, traoe of starting material. 94.51). showing the same ratio of aldehydic products of 95:5; mainly 2’(2-mathoxy-6-naphthyl) ‘H-W d (300 MHz, CDCl,) 1.55 (3H, d, J 7 Hz. CH,). 3.8 (1H. q. J 6 Hz, CH), 3.95 (3H, 7.15 (2H m, Ar), 7.3 (2H, m, ArLr),7.75 (2H, m, Ar). 9.75 (lH, d, J 1 Hz, CHO); m.P. (llt ,.’ 52-7’ ).

Hydrofonnylation catalyxai by rhodium complexes

5109

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