Wang Qing, Tao Xiangzhang, Ni Shengyang, Pan Yi, Wang Yi
State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China.
Org Lett. 2023 Aug 11;25(31):5822-5826. doi: 10.1021/acs.orglett.3c02082. Epub 2023 Jul 31.
Bimolecular nucleophilic substitution S2 is the earliest and most important means of amination of alkyl electrophiles; its practical utilization is largely limited to primary or activated substrates. Furthermore, a persistent challenge lies in establishing C(sp)-N bonds from alkyl substrates in cross-coupling chemistry using palladium and nickel catalysts. Therefore, the methods of constructing C(sp)-N bonds remain rare from alkyl electrophiles. The existing routes are limited to copper catalysis and photoredox catalysis. Here, we demonstrate an alternative amination strategy for rapid construction of C(sp)-N bonds from accessible alkyl electrophiles, which were used as radical precursors under nickel catalysis by Ni (III) species reductive eliminations in high efficiency.
