Journal
ORGANIC LETTERS
Volume 25, Issue 31, Pages 5822-5826Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.3c02082
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Bimolecular nucleophilic substitution S(N)2 is the earliest and most important means of amination of alkyl electrophiles, but its practical utilization is mostly limited to primary or activated substrates. Establishing C(sp(3))-N bonds from alkyl substrates in cross-coupling chemistry using palladium and nickel catalysts has been a persistent challenge. The existing routes are restricted to copper catalysis and photoredox catalysis. In this study, we demonstrate an alternative amination strategy that rapidly constructs C(sp(3))-N bonds from accessible alkyl electrophiles by utilizing Nickel (III) species reductive eliminations under high efficiency catalysis.
Bimolecular nucleophilic substitution S(N)2is the earliestand most important means of amination of alkyl electrophiles; itspractical utilization is largely limited to primary or activated substrates.Furthermore, a persistent challenge lies in establishing C(sp(3))-N bonds from alkyl substrates in cross-coupling chemistryusing palladium and nickel catalysts. Therefore, the methods of constructingC(sp(3))-N bonds remain rare from alkyl electrophiles.The existing routes are limited to copper catalysis and photoredoxcatalysis. Here, we demonstrate an alternative amination strategyfor rapid construction of C(sp(3))-N bonds from accessiblealkyl electrophiles, which were used as radical precursors under nickelcatalysis by Ni (III) species reductive eliminations in high efficiency.
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