Organic Chemistry Portal

Abstracts

Search:

Ru-Catalyzed Hydroboration of Ynones Leads to a Nontraditional Mode of Reactivity

Qiang Feng, Shijia Li, Zhiyang Li, Qiaolin Yan, Xiangfeng Lin, Lijuan Song*, Xinhao Zhang*, Yun-Dong Wu* and Jianwei Sun*

*HIT, Shenzhen 518055; PKU Grad School, Shenzhen 518055; Shenzhen Res. Institute, Shenzhen 518057, China, Email: songlijuanhit.edu.cn, zhangxhpkusz.edu.cn, wuydpkusz.edu.cn, sunjwust.hk

Q. Feng, S. Li, Z. Li, Q. Yan, X. Lin, L. Song, X. Zhang, Y.-D. Wu, J. Sun, J. Am. Chem. Soc., 2022, 144, 14846-14855.

DOI: 10.1021/jacs.2c06024


see article for more reactions

Abstract

A ruthenium-catalyzed hydroboration of ynones provides vinyl α-hydroxylboronates under mild conditions. This reaction features high efficiency, a broad scope, and complete chemo-, regio-, and stereoselectivity, in spite of many possible competitive pathways.

see article for more examples

proposed reaction pathway



Key Words

allylboronates, α-hydroxyboronates, pinacolborane


ID: J48-Y2022