Palladium-catalyzed intermolecular Heck reaction of alkyl halides

被引:108
作者
Zou, Yinjun [1 ]
Zhou, Jianrong [1 ]
机构
[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore
基金
新加坡国家研究基金会;
关键词
ORGANIC HALIDES; RADICAL ALKENYLATION; COUPLING REACTIONS; SIMPLE ALKENES; BROMIDES; BENZYL; ARYL; OLEFINATION; CYCLIZATION; SECONDARY;
D O I
10.1039/c4cc00297k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Intermolecular Heck reaction of common alkyl halides, a long-standing problem in palladium catalysis, is realized with a simple Pd/dppf catalyst. Both primary and secondary alkyl halides are suitable for coupling with aromatic olefins. Single electron transfer from (dppf) Pd-degrees to alkyl halide initiated the catalytic cycle and gave alkyl radicals.
引用
收藏
页码:3725 / 3728
页数:4
相关论文
共 50 条
[31]   Highly regioselective synthesis of spirocyclic compounds by a palladium-catalyzed intermolecular tandem reaction [J].
Bi, Hai-Peng ;
Liu, Xue-Yuan ;
Gou, Ta-Rong ;
Guo, Li-Na ;
Duan, Xin-Hua ;
Shu, Xing-Zhong ;
Liang, Yong-Min .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (37) :7068-7071
[32]   Palladium-Catalyzed Heck Reaction of Polyoxometalate-Functionalised Aryl Iodides and Bromides with Olefins [J].
Zhu, Yulin ;
Wang, Longsheng ;
Hao, Jian ;
Yin, Panchao ;
Zhang, Jin ;
Li, Qiang ;
Zhu, Li ;
Wei, Yongge .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (13) :3076-3080
[33]   Palladium-catalyzed asymmetric dearomative alkenylation of indoles through a reductive-Heck reaction [J].
Liang, Ren-Xiao ;
Yang, Run-Ze ;
Liu, Ren-Rong ;
Jia, Yi-Xia .
ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (11) :1840-1843
[34]   Enantioselective Dicarbofunctionalization of Unactivated Alkenes by Palladium-Catalyzed Tandem Heck/Suzuki Coupling Reaction [J].
Zhang, Zhan-Ming ;
Xu, Bing ;
Wu, Lizuo ;
Wu, Yuanqi ;
Qian, Yanyan ;
Zhou, Lujia ;
Liu, Yu ;
Zhang, Junliang .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (41) :14653-14659
[35]   Progress in Palladium-Catalyzed Amination of Aryl Halides [J].
Fang, Shai ;
Lu, Meixiang ;
Long, Yuhua ;
Yang, Diangqiao .
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2011, 31 (10) :1573-1581
[36]   Palladium-Catalyzed Alkenylation of Azaarylmethylamines with Vinyl Halides [J].
Duan, Shengzu ;
Li, Minyan ;
Ma, Xueqiong ;
Chen, Wen ;
Li, Liang ;
Zhang, Hongbin ;
Yang, Xiaodong ;
Walsh, Patrick J. .
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (24) :4837-4842
[37]   Palladium-Catalyzed Oxidative Heck-Type Alkylation/Aryl Migration/Desulfonylation between Alkenes with α-Carbonyl Alkyl Bromides [J].
Fan, Jian-Hong ;
Yang, Ji ;
Song, Ren-Jie ;
Li, Jin-Heng .
ORGANIC LETTERS, 2015, 17 (04) :836-839
[38]   Oxidative Heck Reaction of Glycals and Aryl Hydrazines: A Palladium-Catalyzed C-Glycosylation [J].
Bai, Yaguang ;
Kim, Le Mai Hoang ;
Liao, Hongze ;
Liu, Xue-Wei .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (17) :8821-8825
[39]   Photoinduced Pd-Catalyzed Intramolecular 6-endo Heck Reaction of Alkyl Halides [J].
Shu, Long ;
Dong, Xu ;
Sun, Ze-Hua ;
Zhao, Anxin ;
Jiang, Mengyao ;
Ren, Xiaomin ;
Yan, Fachao ;
Cao, Kai ;
Liu, Qing ;
Liu, Hui .
ORGANIC LETTERS, 2024, :5719-5724
[40]   Palladium-Catalyzed Intermolecular Polarity-Mismatched Addition of Unactivated Alkyl Radicals to Unactivated Alkenes [J].
Wu, Xiaojin ;
Xiao, Guanlin ;
Ding, Yalan ;
Zhan, Ying ;
Zhao, Yao ;
Chen, Rizhi ;
Loh, Teck-Peng .
ACS CATALYSIS, 2020, 10 (23) :14107-14116