Access to 4-Methylene-phospholenes through BF3•Et2O Catalyzed Isomerization of 3,4-Dimethylphosphole Sulfides

Abstract

We have developed a practical synthetic approach to 4-methylene-phospholene derivatives through BF₃•Et₂O-catalyzed isomerization of 3,4-dimethylphosphole sulfides. The reaction simultaneously establishes a P-stereocenter while performing skeletal rearrangement. The transformation is enabled by the weak antiaromatic character of the phosphole sulfides, which facilitates the thermodynamically favoured migration of endocyclic double bond to exocyclic terminal position.

Supplementary files

Article information

Article type
Communication
Submitted
07 Jun 2025
Accepted
01 Jul 2025
First published
01 Jul 2025

Org. Biomol. Chem., 2025, Accepted Manuscript

Access to 4-Methylene-phospholenes through BF3•Et2O Catalyzed Isomerization of 3,4-Dimethylphosphole Sulfides

M. Xiao, Y. Wang, L. Chen and R. Tian, Org. Biomol. Chem., 2025, Accepted Manuscript , DOI: 10.1039/D5OB00940E

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