Premium
Palladium‐Catalyzed Oxidative Cross‐Coupling of α‐Cyanoketene Dithioacetals with Olefins
Author(s) -
Yang Xiaoge,
Liu Zhuqing,
Sun Chenglin,
Chen Jiping,
Yu Zhengkun
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201502280
Subject(s) - palladium , olefin fiber , catalysis , chemistry , benzoquinone , diene , oxidative coupling of methane , organic chemistry , polymer chemistry , medicinal chemistry , natural rubber
Efficient palladium‐catalyzed cross‐coupling reactions of the internal olefins α‐cyanoketene dithioacetals with a variety of olefins were achieved in dioxane/HOAc/DMSO (9:3:1 v / v / v ) under air atmosphere or by means of AgOAc as the terminal oxidant. Electron‐deficient terminal olefins reacted to form the linear diene derivatives with air as the oxidant. Styrenes underwent the cross‐coupling to give both the linear and branched dienes when using AgOAc as the oxidant. Unactivated cyclic and linear internal olefin substrates both reacted in the presence of a catalytic amount of benzoquinone in air to produce skipped dienes. The typical products were structurally confirmed by X‐ray crystallography.