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

• Main Authors: Li, Xiaohong, Zhang, Dong, Wang, Yan, Xiao, Shiji, Wu, Ying, Xie, Peizhong, Loh, Teck-Peng
• Other Authors: School of Physical and Mathematical Sciences
• Format: Article
• Language: English
• Published: 2024
• Subjects: Chemistry; Allylic Alcohol; Wittig Reaction
• Online Access: https://hdl.handle.net/10356/173495
• Institution: Nanyang Technological University

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.