Palladium-Catalyzed Direct C-H Olefination of Polyfluoroarenes with Alkenyl Tosylates

被引:3
作者
Yee, Ka Yee
Leung, Man Pan
Tse, Man Ho
Choy, Pui Ying
Kwong, Fuk Yee [1 ]
机构
[1] Chinese Univ Hong Kong, Dept Chem, Shatin, Hong Kong, Peoples R China
关键词
Homogeneous catalysis; Olefination; Palladium; Phosphine ligands; Polyfluoroarenes; CROSS-COUPLING REACTIONS; ARYL MESYLATES; HECK REACTION; PHOSPHINE-LIGANDS; DIRECT ARYLATION; SUZUKI; SYSTEM; HETEROARYL;
D O I
10.1002/ejic.202200288
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The first general examples of palladium-catalyzed direct C-H olefination of polyfluoroarenes using alkenyl tosylates as electrophilic coupling partners are presented. By employing the Pd/L1 catalyst system (L1=N-methyl-2-(2',4'-dimethoxyphenyl)-3-dicyclohexylphosphinoindole), the olefinated polyfluoroarenes can be obtained in good-to-excellent yields. Good structural and functional compatibility are also exhibited. In particular, the steric demanding and heterocyclic alkenyl tosylates react smoothly under this catalyst system. This reaction can be practicably performed on a gram-scale without significantly loss of product yields.
引用
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页数:10
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[61]   Preparation of α,β-unsaturated esters and amides via external-CO-free palladium-catalyzed carbonylation of alkenyl tosylates [J].
Ueda, Tsuyoshi ;
Konishi, Hideyuki ;
Manabe, Kei .
TETRAHEDRON LETTERS, 2012, 53 (38) :5171-5175
[62]   Non-Chelate-Assisted Palladium-Catalyzed Aerobic Oxidative Heck Reaction of Fluorobenzenes and Other Arenes: When Does the C-H Activation Need Help? [J].
Villalba, Francisco ;
Albeniz, Ana C. .
ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (20) :4795-4804
[63]   A versatile palladium catalyst system for Suzuki-Miyaura coupling of alkenyl tosylates and mesylates [J].
Wong, Pui Yu ;
Chow, Wing Kin ;
Chung, Kin Ho ;
So, Chau Ming ;
Lau, Chak Po ;
Kwong, Fuk Yee .
CHEMICAL COMMUNICATIONS, 2011, 47 (29) :8328-8330
[64]   When cross-coupling partners meet indolylphosphines [J].
Wong, Shun Man ;
Yuen, On Ying ;
Choy, Pui Ying ;
Kwong, Fuk Yee .
COORDINATION CHEMISTRY REVIEWS, 2015, 293 :158-186
[65]   The Recent Development of Phosphine Ligands Derived from 2-Phosphino-Substituted Heterocycles and Their Applications in Palladium-Catalyzed Cross-Coupling Reactions [J].
Wong, Shun Man ;
So, Chau Ming ;
Kwong, Fuk Yee .
SYNLETT, 2012, (08) :1132-1153
[66]   Thioether-Promoted Direct Olefination of Polyfluoroarenes Catalyzed by Palladium [J].
Wu, Cai-Zhi ;
He, Chun-Yang ;
Huang, Yangen ;
Zhang, Xingang .
ORGANIC LETTERS, 2013, 15 (20) :5266-5269
[67]   Palladium-catalysed mono-α-alkenylation of ketones with alkenyl tosylates [J].
Wu, Yong ;
Fu, Wai Chung ;
Chiang, Chien-Wei ;
Choy, Pui Ying ;
Kwong, Fuk Yee ;
Lei, Aiwen .
CHEMICAL COMMUNICATIONS, 2017, 53 (05) :952-955
[68]   Synthesis and characterization of bent fluorine-containing donor-π-acceptor molecules as intense luminophores with large Stokes shifts [J].
Yamada, Shigeyuki ;
Nishizawa, Akito ;
Morita, Masato ;
Hosokai, Takuya ;
Okabayashi, Yusuke ;
Agou, Tomohiro ;
Hosoya, Takaaki ;
Kubota, Toshio ;
Konno, Tsutomu .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (28) :6911-6919
[69]   A Mild and Efficient Palladium-Catalyzed Cyanation of Aryl Mesylates in Water or tBuOH/Water [J].
Yeung, Pui Yee ;
So, Chau Ming ;
Lau, Chak Po ;
Kwong, Fuk Yee .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (47) :8918-8922
[70]   Selective Palladium-Catalyzed C-F Activation/Carbon-Carbon Bond Formation of Polyfluoroaryl Oxazolines [J].
Yu, Daohong ;
Shen, Qilong ;
Lu, Long .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (04) :1798-1804