CC BY-ND-NC 4.0 · Synthesis 2019; 51(01): 240-250
DOI: 10.1055/s-0037-1610378
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Alkylpotassium-Catalyzed Benzylic C–H Alkylation of Alkylarenes with Alkenes

Io Sato
,
Yasuhiro Yamashita*
Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan   Email: shu_kobayashi@chem.s.u-tokyo.ac.jp   Email: yyamashita@chem.s.u-tokyo.ac.jp
,
Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan   Email: shu_kobayashi@chem.s.u-tokyo.ac.jp   Email: yyamashita@chem.s.u-tokyo.ac.jp
› Author Affiliations
This work was partially supported by ACT-C, JST, and AMED (S.K.), and JSPS KAKENHI Grant Number JP 17H06448 (Y.Y.). I.S. thanks JSPS Research Fellowships for Young Scientists and MERIT program, The University of Tokyo, for financial support.
Further Information

Publication History

Received: 17 October 2018

Accepted: 18 October 2018

Publication Date:
26 November 2018 (eFirst)

Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue

Abstract

Catalytic benzylic C–H alkylation reactions of alkylarenes with alkenes such as β-substituted styrenes and vinylsilanes have been achieved by utilizing alkylpotassium as a catalyst. Various substituted toluene derivatives can be alkylated under mild reaction conditions to afford the desired functionalized hydrocarbons in moderate to high yields.

Supporting Information

 
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