Synthesis 2017; 49(16): 3590-3601
DOI: 10.1055/s-0036-1588464
special topic
© Georg Thieme Verlag Stuttgart · New York

Nickel-Catalyzed Reductive Cross-Coupling of Aryl Triflates and Nonaflates with Alkyl Iodides

Yuto Sumida*
a   Chemical Biology Team, Division of Bio-Function Dynamics Imaging, RIKEN Center for Life Science Technologies, 6-7-3 Minatojima-minamimachi, Chuo-ku, Kobe 650-0047, Japan   Email: takamitsu.hosoya@riken.jp   Email: yuto.sumida@riken.jp
,
Tomoe Sumida
a   Chemical Biology Team, Division of Bio-Function Dynamics Imaging, RIKEN Center for Life Science Technologies, 6-7-3 Minatojima-minamimachi, Chuo-ku, Kobe 650-0047, Japan   Email: takamitsu.hosoya@riken.jp   Email: yuto.sumida@riken.jp
,
a   Chemical Biology Team, Division of Bio-Function Dynamics Imaging, RIKEN Center for Life Science Technologies, 6-7-3 Minatojima-minamimachi, Chuo-ku, Kobe 650-0047, Japan   Email: takamitsu.hosoya@riken.jp   Email: yuto.sumida@riken.jp
b   Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU), 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan   Email: thosoya.cb@tmd.ac.jp
› Author Affiliations
This research was supported by JSPS KAKENHI Grant Number 16K17907 (Y.S.); Japan Prize Foundation (Y.S.); the Incentive Research Grant from RIKEN (Y.S.).
Further Information

Publication History

Received: 31 March 2017

Accepted after revision: 20 May 2017

Publication Date:
28 June 2017 (online)


Dedicated to Professor Teruaki Mukaiyama in celebration of his 90th birthday (Sotsuju­)
Published as part of the Special Topic Advanced Strategies in Synthesis with Nickel

Abstract

A nickel-catalyzed cross-electrophile coupling of aryl triflates and nonaflates with alkyl iodides using manganese(0) as a reductant is described. The method is applicable to the reductive alkylation of various aryl sulfonates, including o-borylaryl triflate, which enabled efficient construction of diverse alkylated arenes under mild conditions.

Supporting Information