title: Palladium-Catalyzed Oxidative Cross-Coupling of α-Cyanoketene Dithioacetals with Olefins.
abstract: 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.
authors.affiliation: Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023 (P. R. China).
authors.forename: Xiaoge
authors.initials: X
authors.lastname: Yang
authors.affiliation: Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023 (P. R. China).
authors.forename: Zhuqing
authors.initials: Z
authors.lastname: Liu
authors.affiliation: Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023 (P. R. China).
authors.forename: Chenglin
authors.initials: C
authors.lastname: Sun
authors.affiliation: Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023 (P. R. China).
authors.forename: Jiping
authors.initials: J
authors.lastname: Chen
authors.affiliation: Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023 (P. R. China). zkyu@dicp.ac.cn.|State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032 (P. R. China). zkyu@dicp.ac.cn.
authors.forename: Zhengkun
authors.initials: Z
authors.lastname: Yu
keywords: CC coupling; CH activation; olefination; palladium; unactivated olefins