期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 17, 页码 6750-6755出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201916014
关键词
alkynes; cobalt; hydrogenation; isomerizations; synthetic methods
资金
- National Natural Science Foundation of China [21702118, 21822106]
- Foundation of the Department of Education of Guangdong Province [2018KZDXM070]
Migratory functionalization of alkenes has emerged as a powerful strategy to achieve functionalization at a distal position to the original reactive site on a hydrocarbon chain. However, an analogous protocol for alkyne substrates is yet to be developed. Herein, a base and cobalt relay catalytic process for the selective synthesis of (Z)-2-alkenes and conjugated E alkenes by migratory hydrogenation of terminal alkynes is disclosed. Mechanistic studies support a relay catalytic process involving a sequential base-catalyzed isomerization of terminal alkynes and cobalt-catalyzed hydrogenation of either 2-alkynes or conjugated diene intermediates. Notably, this practical non-noble metal catalytic system enables efficient control of the chemo-, regio-, and stereoselectivity of this transformation.
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