A C-H Insertion Approach to Functionalized Cyclopentenones

作者：Wang, Youliang; Zarca, Maxence; Gong, Liu-Zhu; Zhang, Liming^*

来源：Journal of the American Chemical Society, 2016, 138(24): 7516-7519.

DOI：10.1021/jacs.6b04297

• CATALYZED CYCLIZATION
• ACTIVATION
• VINYLIDENE
• COMPLEXES

Cyclopentenones are synthetically versatile structures, and their straightforward construction from alkynone substrates by employing synthetically streamlining C-H insertion is conceptually appealing and of high synthetic potential. But, its implementation is very limited. Herein we report a Au-catalyzed version, which affords 2-bromocyclopent-2-en-1-ones with a broad scope and synthetically desirable diastereoselectivities. The proposed key intermediate capable of the observed insertion into unactivated C-H bonds is a fully functionalized gold vinylidene, which is generated via a novel intermolecular strategy. This flexible access of likely gold vinylidenes opens various opportunities to explore their versatile reactivities.

• 出版日期2016-6-22
• 单位中国科学技术大学