Diastereoselective Cyclopropanation of Terminal, Nonconjugated Alkenes with 2-Oxoethylpyridinium Salts via Nucleopalladation

Organic Letters 2026

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Authors: Mandalaparthi Phanindrudu, Zhengzhi Wang, Ting Li, Tesfaye Tebeka Simur, Yingyu Yang, Weijia Lai, Martin G. Banwell, Jia Zheng
DOI: 10.1021/acs.orglett.5c05472
Cited by: 2
References: 68

Abstract

A highly diastereoselective Pd(II)-catalyzed cyclopropanation of terminal, nonconjugated alkenes using 2-oxoethylpyridinium salts as a “carbenoid” source is reported. An AQ-directed nucleopalladation reaction followed by oxidative ring closure and reductive elimination steps results in the formation of a three-membered ring rather than the generation of [3+2] cycloaddition products. The process allows for the ready reaction of a range of 2-oxoethylpyridinium salts with simple olefins and provides an efficient means for the construction of syn -disubstituted cyclopropanes. The protocol is operationally straightforward, scalable and applicable to a wide range of substrates.

Fields of Study & Subjects

Cyclopropane Reaction Mechanisms Catalytic C–H Functionalization Methods Catalytic Alkyne Reactions

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
9
Pages
2871–2876
Publication date
18 February 2026
Language
EN