Synthesis 2017; 49(16): 3726-3730
DOI: 10.1055/s-0036-1588421
paper
© Georg Thieme Verlag Stuttgart · New York

An Efficient and Modular Route to C3*-TunePhos-Type Ligands

Xu Deng
a   College of Chemistry and Molecular Science, Wuhan University, Wuhan, Hubei 430072, P. R. of China   Email: huilv@whu.edu.cn   Email: xumu@whu.edu.cn
b   College of Xiangya Pharmaceutical Sciences, Central South University, Changsha 410013, P. R. of China
,
Yu-Qing Guan
a   College of Chemistry and Molecular Science, Wuhan University, Wuhan, Hubei 430072, P. R. of China   Email: huilv@whu.edu.cn   Email: xumu@whu.edu.cn
,
Ning-Ning Huo
a   College of Chemistry and Molecular Science, Wuhan University, Wuhan, Hubei 430072, P. R. of China   Email: huilv@whu.edu.cn   Email: xumu@whu.edu.cn
,
Ya-Jing Wang
c   Hunan University of Chinese Medicine, Changsha 410208, China
,
Hui Lv*
a   College of Chemistry and Molecular Science, Wuhan University, Wuhan, Hubei 430072, P. R. of China   Email: huilv@whu.edu.cn   Email: xumu@whu.edu.cn
,
Xu-Mu Zhang*
a   College of Chemistry and Molecular Science, Wuhan University, Wuhan, Hubei 430072, P. R. of China   Email: huilv@whu.edu.cn   Email: xumu@whu.edu.cn
d   Department of Chemistry, South University of Science and Technology of China, Shenzhen 518055, P. R. of China
› Author Affiliations
We are grateful for the financial support by a grant from Wuhan University (203273463), ‘111’ Project of the Ministry of Education of China and the National Natural Science Foundation of China (Grant No. 21302193, 21372179, 21432007, 21402145).
Further Information

Publication History

Received: 25 February 2017

Accepted after revision: 17 April 2017

Publication Date:
11 May 2017 (online)


Abstract

An efficient and modular synthetic route to the bidentate C3*-TunePhos was developed, which allowed tunable steric and electronic effects of the ligands. This novel chemical technology highlights a versatile C3*-dibromodiphenyl intermediate that was accomplished by in situ Grignard exchange and subsequent Cu(II)-mediated intra­molecular oxidative radical coupling process. It is worth noting that this advanced intermediate not only could be easily prepared by a diverse array of C3*-TunePhos-type ligands, but also could be used to facile synthesis of other novel type of N,S-centered bidentate ligands.

Supporting Information