Work

Pd‐Catalyzed Regio‐ and Stereoselective Ring‐Opening Hydrosulfonylation of Methylenecyclopropanes for Branched Allylic Sulfones

Year: 2025

Type: article

Abstract: A Pd‐catalyzed ring‐opening hydrosulfonylation reaction of methylenecyclopropanes with sulfonyl hydrazides was developed, which produced a series of branched ( E )‐allylic sulfones in 52−91% yields. In addition, the asymmetric variant was also investigated, and the optically active products were obtained in moderate yields with good enantioselectivities (up to 94:6 er). Mechanistic studies suggested that the reaction proceeds through the formation of an allyl hydrazine intermediate and subsequent rearrangement to the branched ( E )‐allylic sulfone products. Generally, the reaction was completed in one pot under mild reaction conditions, which also featured in good functional group tolerance, broad substrate scope, high regiospecificity, branched selectivity, as well as atom and step economy.

Source: Advanced Synthesis & Catalysis

DOI: 10.1002/adsc.9589

Authors: Bu‐Hong Zhang, Jia‐Xin Song, Bai‐Lin Wang, Zhi‐Xiong Ou, Li‐Bo Li, Xing‐Wang Wang

Institution: Soochow University

Language: English

Topic: Cyclopropane Reaction Mechanisms

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

Funders: National Natural Science Foundation of China, Priority Academic Program Development of Jiangsu Higher Education Institutions, Program for New Century Excellent Talents in University

Awards: G1719562576, G5035575934, G647254767, G7442532631