Fe-Promoted Chlorobenzylation of Terminal Alkynes through Benzylic C(sp(3))-H Bond Functionalization.

Org Lett

Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, China.

Published: March 2016

A chlorobenzylation of terminal alkynes through Fe(II)-promoted benzylic C(sp(3))-H bond functionalization in the presence of NCS as a chloride source was developed. Compared with previous methods to prepare polysubstituted alkenyl halides, the presented procedure provides an efficient alternative with high atom and step economy under mild conditions. The transformation was established to proceed through a single-electron transfer (SET) process with benzyl cations as key intermediates.

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http://dx.doi.org/10.1021/acs.orglett.5b02472DOI Listing

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