Nickel-Catalyzed Reductive Borylation of Enaminones via C(sp<sup>2</sup>)–N Bond Cleavage
Xiaoning Li, Zunsheng Chen, Yan Liu, Nianhua Luo, Weiming Chen, Chenfu Liu, Fuchao Yu, Jiuzhong Huang
Abstract
The cleavage and transformation of alkenyl C(sp2)–N bonds is a significant synthetic challenge. Herein we described an unprecedented nickel-catalyzed reductive borylation of enaminones to synthesize β-ketone boronic esters. Notably, B2pin2 played the dual role in this process, and water served as a hydrogen source, which was transferred to target products. The air-stable nickel catalyst was applied to the cleavage of alkenyl C(sp2)–N bonds, concomitant with the reductive process of the alkenyl boronic ester intermediates, on the basis of the mechanism study.
Topics & Concepts
BorylationCatalysisChemistryNickelBond cleavageCleavage (geology)Reductive eliminationCombinatorial chemistryArylMedicinal chemistryKetoneOrganic chemistryMaterials scienceFracture (geology)Composite materialAlkylCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsOrganoboron and organosilicon chemistry