“Addition–Elimination” Transformations for Aminative Isomerization of Bicyclo[1.1.0]butanes (BCBs)

Organic Letters 2026

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Authors: Shuyu Yang, Jian Chen, Yajun Li, Hongli Bao
DOI: 10.1021/acs.orglett.6c00966
Cited by: 1
References: 66

Abstract

This work discloses a novel aminative isomerization of bicyclo[1.1.0]butanes (BCBs) for the synthesis of functionalized cyclobutenes in which the C═C bond is directly adjacent to the ester group, a previously inaccessible constitutional isomer. The transformation employs sulfonyl sulfur diimides as amination reagents under catalyst-free and mild conditions. Mechanistic studies support an addition-elimination pathway involving a formal [2π+2σ] cycloaddition followed by intramolecular elimination and deprotection.

Fields of Study & Subjects

Radical Photochemical Reactions Cyclopropane Reaction Mechanisms Catalytic C–H Functionalization Methods

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
15
Pages
4899–4904
Publication date
6 April 2026
Language
EN