Solution-Phase and Mechanochemical Brønsted-Acid-Catalyzed N-Alkylation of NH-Heterocycles via Hydroamination of Vinyl Ethers

Organic Letters 2026

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Authors: Vikash Kumar, Rajaram Maayuri, L. N. S. Laya Pagadala, Mahesh Kumar Ravva, Parthasarathy Gandeepan
DOI: 10.1021/acs.orglett.6c00125
Cited by: 2
References: 45

Abstract

A Brønsted-acid-catalyzed hydroamination of vinyl ethers with carbazoles was developed using diphenyl hydrogen phosphate (DPHP) as the catalyst. The method enables the efficient, regioselective N-alkylation of various carbazoles and NH-heterocycles under mild conditions. Mechanistic studies indicate bifunctional activation through hydrogen bonding and cation-π interactions. The reaction was also adapted to mechanochemical conditions for a greener process. While attempts at enantioselective hydroamination have met with limited success, this approach provides a practical and sustainable route to N-alkylated heterocycles.

Fields of Study & Subjects

Crystallography and molecular interactions Axial and Atropisomeric Chirality Synthesis Vanadium and Halogenation Chemistry

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
21
Pages
6503–6508
Publication date
28 January 2026
Language
EN