Synthesis 2024; 56(24): 3923-3928
DOI: 10.1055/s-0043-1775414
paper
Special Topic Dedicated to Prof. Erick Carreira

Olefination of Activated Alkyl Halides with Phosphonium Salts

Sven Roediger
,
,
Cosima L. Brudy
,
Mischa Trabesinger
,
Jan Hübscher
,
Bill Morandi
The European Research Council (Shuttle Cat, Project ID: 757608), ETH Zürich, and the FCI (scholarships to S.R. and C.L.B.) are acknowledged for funding of this work.


Dedicated to Prof. Erick M. Carreira on the occasion of his 60th birthday.

Abstract

A base-promoted olefination reaction between alkylphosphonium salts and activated alkyl halides has been developed. The products were obtained in excellent E-selectivity. In contrast to most other olefination reactions of phosphonium salts, the reaction yields triphenylphosphine as the main by-product, which can be directly reused in the formation of new phosphonium salts.

Supporting Information



Publication History

Received: 03 July 2024

Accepted after revision: 08 October 2024

Article published online:
07 November 2024

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