Palladium-Catalyzed 1,3-Difunctionalization Using Terminal Alkenes with Alkenyl Nonaflates and Aryl Boronic Acids
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- 作者：Matthew S. McCammant ; Takashi Shigeta ; Matthew S. Sigman
- 刊名：Organic Letters
- 出版年：2016
- 出版时间：April 15, 2016
- 年：2016
- 卷：18
- 期：8
- 页码：1792-1795
- 全文大小：408K
- 年卷期：0
- ISSN：1523-7052
文摘
A Pd-catalyzed 1,3-difunctionalization of terminal alkenes using 1,1-disubstituted alkenyl nonaflates and arylboronic acid coupling partners is reported. This transformation affords allylic arene products that are difficult to selectively access using traditional Heck cross-coupling methodologies. The evaluation of seldom employed 1,1-disubstituted alkenyl nonaflate coupling partners led to the elucidation of subtle mechanistic features of π-allyl stabilized Pd-intermediates. Good stereo- and regioselectivity for the formation of 1,3-addition products can be accessed through a minimization of steric interactions that emanate from alkenyl nonaflate substitution.