Palladium-Catalyzed Stereoselective C-F Bond Vinylation and Allylation of Tetrasubstituted gem-Difluoroalkenes via Stille Coupling: Synthesis of Monofluorinated 1,3-and 1,4-Dienes

被引：11
|
作者：
Li, Min [1 ]
Wang, Yanhui [1 ]
Tsui, Gavin Chit [1 ]
机构：
[1] Chinese Univ Hong Kong, Dept Chem, Shatin, Hong Kong 999077, Peoples R China
来源：
ORGANIC LETTERS | 2021年 / 23卷 / 20期
关键词：
ACTIVATION;
D O I：
10.1021/acs.orglett.1c03096
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We herein describe a Pd-catalyzed stereoselective C-F bond vinylation and allylation reaction of tetrasubstituted gem-difluoroalkenes for the synthesis of valuable monofluorinated 1,3- and 1,4-dienes with excellent diastereoselectivities. Different from previously used Pd(PPh3)(4), a catalytic system involving Pd(0) and dppe as the ligand was developed for Stille-type cross-coupling between gem-difluoroalkenes and vinyl- and allyltin reagents.
引用
收藏
页码：8072 / 8076
页数：5
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  • [3] Palladium-Catalyzed Stereoselective Defluorosilylation of gem-Difluoroalkenes for the Synthesis of Tetrasubstituted Monofluorinated Vinylsilanes
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  • [4] Stereoselective Palladium-Catalyzed C–F Bond Alkynylation of Tetrasubstituted gem-Difluoroalkenes
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  • [5] Stereoselective Palladium-Catalyzed C-F Bond Alkenylation of Tetrasubstituted gem-Difluoroalkenes via Mizoroki-Heck Reaction
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  • [6] Stereodivergent Palladium-Catalyzed C-F Bond Functionalization of gem-Difluoroalkenes
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  • [8] Regioselective Synthesis of 1,4-Dienes via Palladium-Catalyzed Oxidative Allylation of N-Tosylhydrazones
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  • [10] Synthesis of gem-Difluoroalkenes via Nickel-Catalyzed Reductive C-F and C-O Bond Cleavage
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