The Fukuyama reduction is an

organic reaction Organic reactions are chemical reactions involving organic compounds. The basic organic chemistry reaction types are addition reactions, elimination reactions, substitution reactions, pericyclic reactions, rearrangement reactions, mechanistic organ ...

and an

organic reduction Organic reductions or organic oxidations or organic redox reactions are redox reactions that take place with organic compounds. In organic chemistry oxidations and reductions are different from ordinary redox reactions, because many reactions car ...

in which a

thioester In organic chemistry, thioesters are organosulfur compounds with the molecular structure . They are analogous to carboxylate esters () with the sulfur in the thioester replacing oxygen in the carboxylate ester, as implied by the thio- prefix ...

is reduced to an

aldehyde In organic chemistry, an aldehyde () (lat. ''al''cohol ''dehyd''rogenatum, dehydrogenated alcohol) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred ...

by a silyl hydride in presence of a

catalytic Catalysis () is the increase in reaction rate, rate of a chemical reaction due to an added substance known as a catalyst (). Catalysts are not consumed by the reaction and remain unchanged after it. If the reaction is rapid and the catalyst ...

amount of

palladium Palladium is a chemical element; it has symbol Pd and atomic number 46. It is a rare and lustrous silvery-white metal discovered in 1802 by the English chemist William Hyde Wollaston. He named it after the asteroid Pallas (formally 2 Pallas), ...

. This reaction was invented in 1990 by

Tohru Fukuyama is a Japanese organic chemist and Professor of Chemistry at University of Tokyo in Japan. He discovered the Fukuyama coupling in 1998. Biography Fukuyama studied chemistry at Nagoya University with degrees Bachelor's (1971) and Master's (1973) ...

. 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 acid In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an Substituent, R-group. The general formula of a carboxylic acid is often written as or , sometimes as with R referring to an organyl ...

s (as thioester precursor) to aldehydes which is considered a difficult procedure because of the ease of secondary reduction to an

alcohol Alcohol may refer to: Common uses * Alcohol (chemistry), a class of compounds * Ethanol, one of several alcohols, commonly known as alcohol in everyday life ** Alcohol (drug), intoxicant found in alcoholic beverages ** Alcoholic beverage, an alco ...

Reaction mechanism

The basic

reaction mechanism In chemistry, a reaction mechanism is the step by step sequence of elementary reactions by which overall chemical reaction occurs. A chemical mechanism is a theoretical conjecture that tries to describe in detail what takes place at each stage ...

for this reaction takes place as a

catalytic cycle In chemistry, a catalytic cycle is a multistep reaction mechanism that involves a catalyst. The catalytic cycle is the main method for describing the role of catalysts in biochemistry, organometallic chemistry, bioinorganic chemistry, materials s ...

: * Oxidative addition: *: + Pd^0 -> RC(O)-Pd^-SR *

Transmetallation Transmetalation (alt. spelling: transmetallation) is a type of organometallic reaction that involves the transfer of ligands from one metal to another. It has the general form: :M1–R + M2–R′ → M1–R′ + M2–R where R and R′ can be, but ...

: *: + R3SiH -> + R3Si-SR * Reductive elimination: *: RC(O)-Pd^-H -> + Pd^0

Scope

In a variation of the Fukuyama reduction the core BODIPY molecule has been synthesized from the SMe-substituted derivative:''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
Additional reagents are copper(I)-thiophene-2-carboxylate (CuTC), Pd(dba)2 and tri(2-furyl)phosphine : BODIPY synthesis Arroyo 2009

In the related

Fukuyama coupling The Fukuyama coupling is a coupling reaction taking place between a thioester and an organozinc halide in the presence of a palladium catalyst. The reaction product is a ketone. This reaction was discovered by Tohru Fukuyama et al. in 1998. Adv ...

the hydride is replaced by a

carbon nucleophile In chemistry, a nucleophile is a chemical species that forms bonds by donating an electron pair. All molecules and ions with a free pair of electrons or at least one pi bond can act as nucleophiles. Because nucleophiles donate electrons, they are ...

References

{{Organic reactions Organic reduction reactions Name reactions