Journal
ORGANIC PROCESS RESEARCH & DEVELOPMENT
Volume 15, Issue 6, Pages 1236-1242Publisher
AMER CHEMICAL SOC
DOI: 10.1021/op200195m
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Funding
- Robert A. Welch Foundation [F-0038]
- NIH-NIGMS [RO1-GM069445]
- Eli Lilly and Company
- Merck
- Johnson and Johnson
- Firmenich
- Umicore
- Takasago
- ACS-GCI
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Hydrogenation of pi-unsaturated reactants in the presence of carbonyl compounds or imines promotes reductive C-C coupling, providing a byproduct-free alternative to stoichiometric organometallic reagents in an ever-increasing range of C=X (X = O, NR) additions. Under transfer hydrogenation conditions, hydrogen exchange between alcohols and pi-unsaturated reactants triggers generation of electrophile nucleophile pairs, enabling carbonyl addition directly from the alcohol oxidation level, bypassing discrete alcohol oxidation and generation of stoichiometric byproducts.
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