Nickel-catalyzed enantioselective 1,2-vinylboration of styrenes

Yang Ye; Jiandong Liu; Bing Xu; Songwei Jiang; Renren Bai; Shijun Li; Tian Xie; Xiang-Yang Ye

doi:10.1039/d1sc04071e

Nickel-catalyzed enantioselective 1,2-vinylboration of styrenes

Chem Sci. 2021 Sep 7;12(39):13209-13215. doi: 10.1039/d1sc04071e. eCollection 2021 Oct 13.

Authors

Yang Ye^{1

2}, Jiandong Liu³, Bing Xu^{1

2}, Songwei Jiang^{1

2}, Renren Bai^{1

2}, Shijun Li⁴, Tian Xie^{1

2}, Xiang-Yang Ye^{1

2}

Affiliations

¹ School of Pharmacy, Hangzhou Normal University Hangzhou Zhejiang 311121 PR China yeyang0711@163.com xbs@hznu.edu.cn xyye@hznu.edu.cn.
² Key Laboratory of Elemene Class Anti-Cancer Chinese Medicines, Engineering Laboratory of Development and Application of Traditional Chinese Medicines, Collaborative Innovation Center of Traditional Chinese Medicines of Zhejiang Province, Hangzhou Normal University Hangzhou Zhejiang 311121 PR China.
³ Center for Supramolecular Chemistry and Catalysis, Department of Chemistry, Shanghai University Shanghai 200444 PR China.
⁴ College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University Hangzhou Zhejiang 311121 PR China.

Abstract

A novel nickel-catalyzed asymmetric 1,2-vinylboration reaction has been developed to afford benzylic alkenylboration products with high yields and excellent enantioselectivities by using a chiral bisoxazoline ligand. Under optimized conditions, a wide variety of chiral 2-boryl-1,1-arylvinylalkanes are efficiently prepared from readily available olefins and vinyl halides in the presence of bis(pinacolato)diboron as the boron source in a mild and easy-to-operate manner. This three-component cascade protocol furnishes exceptional chemo- and stereoselectivity, and its usefulness is illustrated by its application in asymmetric modifications of several structurally complex natural products and pharmaceuticals.