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Copper‐Catalyzed Aerobic Oxidative Transformation of Ketone‐Derived N ‐Tosyl Hydrazones: An Entry to Alkynes
Author(s) -
Li Xianwei,
Liu Xiaohang,
Chen Huoji,
Wu Wanqing,
Qi Chaorong,
Jiang Huanfeng
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201405058
Subject(s) - chemistry , ketone , regioselectivity , hydrazone , deprotonation , catalysis , moiety , oxidative coupling of methane , conjugated system , carbene , triple bond , combinatorial chemistry , oxidative phosphorylation , alkyne , functional group , medicinal chemistry , organic chemistry , double bond , ion , biochemistry , polymer
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 CC triple bond formation.