TY - JOUR
T1 - A direct reduction of aliphatic aldehyde, acyl chloride, ester, and carboxylic functions into a methyl group
AU - Gevorgyan, V.
AU - Rubin, M.
AU - Liu, J. X.
AU - Yamamoto, Y.
PY - 2001/3/9
Y1 - 2001/3/9
N2 - 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.
AB - 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.
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U2 - 10.1021/jo001258a
DO - 10.1021/jo001258a
M3 - Article
C2 - 11262111
AN - SCOPUS:0035831090
SN - 0022-3263
VL - 66
SP - 1672
EP - 1675
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 5
ER -