Journal
SYNLETT
Volume 26, Issue 14, Pages 2037-2041Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0034-1378846
Keywords
alcohols; aldehydes; hydrogenation; NADH analogues; organoboranes
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Funding
- JST-ACCEL program
- JST-CREST program
- Grants-in-Aid for Scientific Research [26620090] Funding Source: KAKEN
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We have developed a method for the hydrogenation of unactivated aldehydes, using a Hantzsch ester as a NAD(P)H analogue in the presence of an electron-deficient triarylborane as a Lewis acid catalyst. Thus, tris[3,5-bis(trifluoromethyl)phenyl]borane efficiently catalyzes the hydrogenation of aliphatic aldehydes with a Hantzsch ester in 1,4-dioxane at 100 degrees C to give the corresponding aliphatic primary alcohols in up to 97% yield. Aromatic aldehydes also undergo the hydrogenation, even at 25 degrees C, to furnish the corresponding aromatic primary alcohols in up to 100% yield.
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