Michael-Addition-Triggered Release of Substituents from Tertiary Amines

Organic Letters 2026

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Authors: Toshiaki Wayama, Hiroki Oguri
DOI: 10.1021/acs.orglett.5c04986
Cited by: 0
References: 33

Abstract

A general and operationally simple method for removing substituents from tertiary amines via Michael-addition-triggered carbocation release is described. Using methyl propiolate, hexafluoroisopropyl alcohol (HFIP), and thioanisole, this reaction enables efficient, metal-free cleavage of challenging groups─including benzyl, p -methoxybenzyl (PMB), allyl, propargyl, diphenylmethyl, and tert -butyl. This carbocation-mediated platform offers predictable, broad-scope amine deprotection and provides a practical alternative to hydrogenolysis and other redox-based protocols.

Fields of Study & Subjects

Asymmetric Hydrogenation and Catalysis Advanced Synthetic Organic Chemistry Catalytic C–H Functionalization Methods

Publication details

Journal / source
Organic Letters
Volume
28
Issue
3
Pages
982–987
Publication date
8 January 2026
Language
EN