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Regio-Selective C3- and N-Alkylation of Indolines in Water under Air Using Alcohols

Milan Maji, Ishani Borthakur, Sameer Srivastava and Sabuj Kundu*

*Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur 208016, Uttar Pradesh, India, Email:

M. Maji, I. Borthakur, S. Srivastava, S. Kundu, J. Org. Chem., 2022, 87, 5603-5616.

DOI: 10.1021/acs.joc.1c03040

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Iridium-catalyzed tandem dehydrogenation of N-heterocycles and alcohols enables regio-selective C-H and N-H bond functionalizations of indolines to provide a diverse range of N- and C3-alkylated indolines/indoles. The practical applicability of this methodology was demonstrated by the preparative-scale synthesis and synthesis of a psychoactive drug, N,N-dimethyltryptamine.

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proposed mechanism

Key Words

indolines, indoles, oxygen

ID: J42-Y2022