Synlett 2015; 26(06): 716-724
DOI: 10.1055/s-0034-1379939
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© Georg Thieme Verlag Stuttgart · New York

Challenges in the Substitution of Terminal C–C Double Bonds with Tertiary Alkyl groups

Takashi Nishikata*
Graduate School of Science and Engineering, Yamaguchi University, 2-16-1 Tokiwadai, Ube, Yamaguchi, 755-8611, Japan   Email: nisikata@yamaguchi-u.ac.jp
,
Shingo Ishikawa
Graduate School of Science and Engineering, Yamaguchi University, 2-16-1 Tokiwadai, Ube, Yamaguchi, 755-8611, Japan   Email: nisikata@yamaguchi-u.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 23 October 2014

Accepted after revision: 26 November 2014

Publication Date:
13 January 2015 (online)

Abstract

There are a few reports on the reaction of tertiary alkyl halide and alkene to produce an alkyl-substituted alkene. To establish tertiary alkylation of a C–C double bond, radical reaction is found to be one of the most promising protocols. In this paper, we highlight tertiary alkyl substitutions on C–C double bonds via atom-transfer radical substitution (ATRS) catalyzed by a copper salt and introduce the corresponding M–H reactions.

1 Alkylation via the Mizoroki–Heck Reaction

2 Tertiary Alkylative M–H-Type Reaction

3 Regioselective Double-Bond Formation

4 Summary and Perspectives

 
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