A C-H Insertion Approach to Functionalized Cyclopentenones.
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.
Department of Chemistry and Biochemistry, University of California , Santa Barbara, California 93106, United States.
Youliang
Y
Wang
Department of Chemistry and Biochemistry, University of California , Santa Barbara, California 93106, United States.
Maxence
M
Zarca
Hefei National Laboratory for Physical Sciences at Microscale and Department of Chemistry, University of Science and Technology of China , Hefei 230026, China.
Liu-Zhu
LZ
Gong
Department of Chemistry and Biochemistry, University of California , Santa Barbara, California 93106, United States.
Liming
L
Zhang