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Nickel-Catalyzed 1,2-Carboamination of Alkenyl Alcohols

submitted on 12.03.2021, 01:33 and posted on 16.03.2021, 10:50 by Taeho Kang, Nana Kim, Peter Cheng, Hao Zhang, Klement Foo, Keary Engle
An alcohol-directed, nickel-catalyzed three-component umpolung carboamination of unactivated alkenes with aryl/alkenylboronic esters and electrophilic aminating reagents is reported. This transformation is enabled by specifically tailored O-(2,6-dimethoxybenzoyl)hydroxylamine electrophiles that suppress competitive processes, including undesired β-hydride elimination and transesterification between the alcohol substrate and electrophile. The reaction delivers the desired 1,2-carboaminated products with excellent regio- and diastereoselectivity and exhibits a broad scope of coupling partners and alkenes, including complex natural products. Various mechanistic experiments and analysis of the stereochemical outcome with a cyclic alkene substrate, as confirmed by X-ray crystallographic analysis, support alcohol-directed syn-insertion of an organonickel(I) species.



Kwanjeong Educational Foundation


Email Address of Submitting Author


The Scripps Research Institute


United States

ORCID For Submitting Author


Declaration of Conflict of Interest

No conflict of interest to declare.