期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 53, 期 52, 页码 14485-14489出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201405058
关键词
aerobic oxidation; alkynes; copper-catalyzed; cross-coupling; ketones
资金
- National Basic Research Program of China (973 Program) [2011CB808600]
- National Natural Science Foundation of China [21172076]
- Guangdong Natural Science Foundation [10351064101000000]
- Fundamental Research Funds for the Central Universities [2014ZP0004]
A novel strategy involving Cu-catalyzed oxidative transformation of ketone-derived hydrazone moiety to various synthetic valuable internal alkynes and diynes has been developed. This method features inexpensive metal catalyst, green oxidant, good functional group tolerance, high regioselectivity and readily available starting materials. Oxidative deprotonation reactions were carried out to form internal alkynes and symmetrical diynes. Cross-coupling reactions of hydrazones with halides and terminal alkynes were performed to afford functionalized alkynes and unsymmetrical conjugated diynes. A mechanism proceeding through a Cu-carbene intermediate is proposed for the C-C triple bond formation.
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