Regioselective Hydroboration and Hydrosilylation of N‑Heteroarenes Catalyzed by a Zinc Alkyl Complex

Xinxin Wang, Yu Zhang, Dan Yuan^*（袁丹）, and Yingming Yao^*（姚英明）

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, People’s Republic of China

Org. Lett. 2020, 22, 5695--5700

Readily available zinc alkyl complexes showed good activity and regioselectivity in catalyzing hydroboration and hydrosilylation of N-heteroarenes. Hydroboration of benzo-fused N-heterocycles gave exclusive 1,2-addition products in 80–97% yields. Reactions of pyridines afforded a mixture of 1,2-, 1,4-, and 1,6-products in yields of 55–95%, with 1,2-dihydropyridine as the main product. Bis-hydrosilylation was observed for quinoline derivatives, generating bis-1,2-hydrosilylation products in 76–96% yields. Kinetic studies and control experiments were conducted to gain some insights into the reaction mechanism.

链接：https://pubs.acs.org/doi/10.1021/acs.orglett.0c02082