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Dehydrative Synthesis of Functionalized Skipped Dienes from Stabilized Phosphonium Ylides and Allylic Alcohols in Water
Author(s) -
Ma Xiantao,
Yu Jing,
Han Cuijie,
Zhou Qiuju,
Ren Mengjuan,
Li Lixin,
Tang Lin
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201801266
Subject(s) - phosphonium , chemistry , allylic rearrangement , alkyl , regioselectivity , alkylation , aryl , organic chemistry , catalysis , medicinal chemistry , photochemistry
A mild and extra activator‐free dehydrative alkylation of stabilized phosphonium ylides with allylic alcohols in water is developed in the presence of [Pd(allyl)Cl] 2 /dppf catalyst. A wide range of aryl, heteroaryl, alkyl and even allylic tertiary alcohols can readily react with stabilized phosphonium ylides with high regioselectivity for the efficient synthesis of functionalized skipped dienes in moderate to high yields. The role of water was investigated by means of a high‐resolution mass spectrum and diffusion‐ordered spectroscopy nuclear magnetic resonance, and the results revealed that water might play a crucial role in the formation of the π‐allylpalladium complex via hydrogen bond. However, the present method is not suitable for water‐sensitive phosphonium ylides.