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The method demonstrates the utility of diazoesters as oxidants in generating α-amino radicals from alkyl aryl tertiary amines, suggesting innovative synthesis pathways.
We report the synthesis of functionalized indolines via α-amino radical/iminium ion through the visible-light-induced SET and HAT mediated [4 + 1]-annulation strategy between alkyl aryl tertiary amines and diazoesters. The unique role of diazoester in this process is as an oxidant for SET generation of aminium ions; it serves as a HAT reagent/deprotonation to form the α-amino radical/iminium ion, and is a reactant to access the functionalized indolines. Mechanistic studies support the proposed mechanism well, and the synthetic utility has also been demonstrated.
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Babbar et al. (2025) studied this question.
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