A direct reduction of aliphatic aldehyde, acyl chloride, ester, and carboxylic functions into a methyl group

V. Gevorgyan, M. Rubin, J. X. Liu, Y. Yamamoto

Research output: Contribution to journalArticle

126 Citations (Scopus)

Abstract

The aliphatic carboxylic group was efficiently reduced to the methyl group by HSiEt3 in the presence of catalytic amounts of B(C6F5)3. To the best of our knowledge, this is the first example of a direct exhaustive reduction of aliphatic carboxylic function. Aliphatic aldehydes, acyl chlorides, anhydrides, and esters also underwent complete reduction under similar reaction conditions. Aromatic carboxylic acids, as well as other carbonyl functional equivalents, underwent smooth partial reduction to the corresponding TES-protected benzylic alcohols. It was shown that, unlike the reduction of aliphatic substrates, the exhaustive reduction of aromatic substrates was not straightforward: a concurrent Friedel-Crafts-like alkylation process competed with the reduction yielding trace to notable amounts of dimeric products, thus decreasing the overall selectivity of the reduction process.

Original languageEnglish (US)
Pages (from-to)1672-1675
Number of pages4
JournalJournal of Organic Chemistry
Volume66
Issue number5
DOIs
StatePublished - Mar 9 2001
Externally publishedYes

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Aldehydes
Chlorides
Esters
Anhydrides
Alkylation
Substrates
Carboxylic Acids
Carboxylic acids
Alcohols

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

A direct reduction of aliphatic aldehyde, acyl chloride, ester, and carboxylic functions into a methyl group. / Gevorgyan, V.; Rubin, M.; Liu, J. X.; Yamamoto, Y.

In: Journal of Organic Chemistry, Vol. 66, No. 5, 09.03.2001, p. 1672-1675.

Research output: Contribution to journalArticle

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