Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 27, Pages 8250-8254Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201802533
Keywords
conjugation; gold; ligand design; reaction mechanisms; synthetic methods
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Funding
- China Scholarship Council
- NIGMS [R01GM123342]
- NIH [S10OD012077]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM123342] Funding Source: NIH RePORTER
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Using the previously designed biphenyl-2-ylphosphine ligand, featuring a remote tertiary amino group, the first gold-catalyzed intermolecular hydroalkenylation of alkynes has been developed. Synthetically valuable conjugated dienyl alcohols are formed in moderate to good yields. A range of alkenyltrifluoroborates are allowed as the alkenyl donor, and no erosion of alkene geometry and/or the propargylic configuration are detected. DFT calculations confirm the critical role of the remote basic group in the ligand as a general-base catalyst for promoting this novel gold catalysis with good efficiency.
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