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F r o m W i k i p e d i a , t h e f r e e e n c y c l o p e d i a
The Fukuyama reduction is an organic reaction and an organic reduction in which a thioester is reduced to an aldehyde by a silyl hydride in presence of a catalytic amount of palladium . This reaction was invented in 1990 by Tohru Fukuyama .[1] In the original scope of the reaction the silyl hydride was triethylsilane and the catalyst palladium on carbon :
Fukuyama reductions are used for the conversion of carboxylic acids (as thioester precursor) to aldehydes which is considered a difficult procedure because of the ease of secondary reduction to an alcohol .
Reaction mechanism [ edit ]
The basic reaction mechanism for this reaction takes place as a catalytic cycle :
Oxidative addition :
R
−
C
(
O
)
−
SR
+
Pd
0
⟶
RC
(
O
)
−
Pd
II
−
SR
{\displaystyle {\ce {{R-C(O )-SR}+ Pd^0 -> RC(O )-Pd^{II}-SR}}}
Transmetallation :
RC
(
O
)
−
Pd
II
−
SR
+
R
3
SiH
⟶
RC
(
O
)
−
Pd
II
−
H
+
R
3
Si
−
SR
{\displaystyle {\ce {{RC(O )-Pd^{II}-SR}+R3SiH->{RC(O )-Pd^{II}-H}+R3Si-SR}}}
Reductive elimination :
RC
(
O
)
−
Pd
II
−
H
⟶
RC
(
O
)
−
H
+
Pd
0
{\displaystyle {\ce {RC(O )-Pd^{II}-H -> {RC(O )-H}+ Pd^0}}}
In a variation of the Fukuyama reduction the core BODIPY molecule has been synthesized from the SMe-substituted derivative:[2] Additional reagents are copper(I )-thiophene-2-carboxylate (CuTC), Pd(dba)2 and tri(2-furyl)phosphine
In the related Fukuyama coupling the hydride is replaced by a carbon nucleophile .
References [ edit ]
^ Facile reduction of ethyl thiol esters to aldehydes: application to a total synthesis of (+)-neothramycin A methyl ether Tohru Fukuyama, Shao Cheng Lin, Leping Li J. Am. Chem. Soc. , 1990, 112 (19 ), pp 7050–7051 doi :10.1021/ja00175a043
^ The Smallest and One of the Brightest. Efficient Preparation and Optical Description of the Parent Borondipyrromethene System. I. J. Arroyo, R. Hu, G. Merino, B. Z. Tang, E. Peña-Cabrera, J. Org. Chem. 2009, ASAP
R e t r i e v e d f r o m " https://en.wikipedia.org/w/index.php?title=Fukuyama_reduction&oldid=1172402936 "
C a t e g o r i e s :
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H i d d e n c a t e g o r i e s :
● A r t i c l e s w i t h s h o r t d e s c r i p t i o n
● S h o r t d e s c r i p t i o n m a t c h e s W i k i d a t a
● T h i s p a g e w a s l a s t e d i t e d o n 2 6 A u g u s t 2 0 2 3 , a t 2 1 : 2 1 ( U T C ) .
● T e x t i s a v a i l a b l e u n d e r t h e C r e a t i v e C o m m o n s A t t r i b u t i o n - S h a r e A l i k e L i c e n s e 4 . 0 ;
a d d i t i o n a l t e r m s m a y a p p l y . B y u s i n g t h i s s i t e , y o u a g r e e t o t h e T e r m s o f U s e a n d P r i v a c y P o l i c y . W i k i p e d i a ® i s a r e g i s t e r e d t r a d e m a r k o f t h e W i k i m e d i a F o u n d a t i o n , I n c . , a n o n - p r o f i t o r g a n i z a t i o n .
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