Convergent Synthesis of Functionalized Indolines from Alkyl Aryl Tertiary Amines and Diazoesters via Visible
Akanksha Babbar1, Mohammad Saleem1, Dongari Yadagiri1
1Laboratory of Organic Synthesis and Catalysis, Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee, Uttarakhand-247667, India.
Abstract:
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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