Issue 40, 2023

Calcium-catalyzed dehydrative allylation of P-ylides and sequential Wittig reaction for streamlined access to versatile 1,4-dienes

Abstract

A transition metal-free dehydrative allylation of stabilized P-ylides with activated allylic alcohols has been developed. This protocol utilizes a calcium catalyst to facilitate the cleavage of C–OH bonds and enables smooth dehydrative cross-coupling with P-ylides, resulting in water as the sole by-product. Remarkably, this transformation exhibits excellent tolerance towards a diverse range of allylic alcohols and P-ylides. Furthermore, the subsequent Wittig reaction affords a wide array of highly functionalized 1,4-dienes with high yields.

Graphical abstract: Calcium-catalyzed dehydrative allylation of P-ylides and sequential Wittig reaction for streamlined access to versatile 1,4-dienes

Supplementary files

Article information

Article type
Paper
Submitted
04 Aug 2023
Accepted
18 Sep 2023
First published
19 Sep 2023

New J. Chem., 2023,47, 18779-18784

Calcium-catalyzed dehydrative allylation of P-ylides and sequential Wittig reaction for streamlined access to versatile 1,4-dienes

X. Li, D. Zhang, Y. Wang, S. Xiao, Y. Wu, P. Xie and T. Loh, New J. Chem., 2023, 47, 18779 DOI: 10.1039/D3NJ03640E

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