Carbene‐Catalyzed Intermolecular Dehydrogenative Coupling of Aldehydes with C(sp<sup>3</sup>)−H Bonds
SU Fen, Juan Zou, Xiaokang Lv, Fengfei Lu, Yijie Long, Kun Tang, Benpeng Li, Huifang Chai, Xingxing Wu, Yonggui Robin
Abstract
Abstract The development of catalyst‐controlled methods for direct functionalization of two distinct C−H bonds represents an appealing approach for C−C formations in synthetic chemistry. Herein, we describe an organocatalytic approach for straightforward acylation of C(sp 3 )−H bonds employing readily available aldehyde as “acyl source” involving dehydrogenative coupling of aldehydes with ether, amine, or benzylic C(sp 3 )−H bonds. The developed method affords a broad range of ketones under mild conditions. Mechanistically, simple ortho ‐cyanoiodobenzene is essential in the oxidative radical N‐heterocyclic carbene catalysis to give a ketyl radical and C(sp 3 ) radical through a rarely explored intermolecular hydrogen atom transfer pathway, rendering the acylative C−C formations in high efficiency under a metal‐ and light‐free catalytic conditions. Moreover, the prepared products show promising anti‐bacterial activities that shall encourage further investigations on novel agrochemical development.