Journal
CHEMISTRY LETTERS
Volume 37, Issue 11, Pages 1102-1107Publisher
CHEMICAL SOC JAPAN
DOI: 10.1246/cl.2008.1102
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Funding
- Merck
- Umicore
- Robert A. Welch Foundation
- ACS-GCI Pharmaceutical Roundtable
- Donald D. Harrington Fellows Program
- NIH-NIGMS [RO1-GM069445]
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Under the conditions of ruthenium-catalyzed transfer hydrogenation employing isopropyl alcohol as terminal reductant, pi-unsaturated compounds (1,3-dienes, allenes, 1,3-enynes, and alkynes) reductively couple to aldehydes to furnish products of carbonyl addition. In the absence of isopropyl alcohol, pi-unsaturated compounds couple directly from the alcohol oxidation level to form identical products of carbonyl addition. Such alcohol-unsaturate C-C couplings enable carbonyl allylation propargylation and vinylation from the alcohol oxidation level in the absence of stoichiometric organometallic reagents or metallic reductants. Thus, direct catalytic C-H functionalization of alcohols at the carbinol carbon is achieved.
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