Ni-Catalyzed Reductive Allylation of α-Chloroboronates to Access Homoallylic Boronates

Yixian Lou; Jian Qiu; Kai Yang; Feng Zhang; Chenglan Wang; Qiuling Song

doi:10.1021/acs.orglett.1c01213

Ni-Catalyzed Reductive Allylation of α-Chloroboronates to Access Homoallylic Boronates

Org Lett. 2021 Jun 18;23(12):4564-4569. doi: 10.1021/acs.orglett.1c01213. Epub 2021 Jun 1.

Authors

Yixian Lou¹, Jian Qiu², Kai Yang², Feng Zhang², Chenglan Wang¹, Qiuling Song^{1

2

3}

Affiliations

¹ Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou, Zhejiang 310014, China.
² Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fuzhou, Fujian 350108, China.
³ Institute of Next Generation Matter Transformation, College of Materials Science Engineering at Huaqiao University, Xiamen, Fujian 361021, China.

PMID: 34061544
DOI: 10.1021/acs.orglett.1c01213

Abstract

The transition-metal-catalyzed allylation reaction is an efficient strategy for the construction of new carbon-carbon bonds alongside allyl or homoallylic functionalization. Herein we describe a Ni-catalyzed reductive allylation of α-chloroboronates to efficiently render the corresponding homoallylic boronates, which could be readily converted into valuable homoallylic alcohols or amines or 1,4-diboronates. This reaction features a broad substrate scope with good functional group compatibility that is complementary to the existing methods for the preparation of homoallylic boronates.