Visible Light Accelerated Vinyl C-H Arylation in Pd-Catalysis: Application in the Synthesis of ortho Tetra-substituted Vinylarene Atropisomers

被引：41

作者：

Feng, Jia ^{[1
]}

Li, Bin ^{[1
]}

Jiang, Julong ^{[1
]}

Zhang, Mingkai ^{[1
]}

Ouyang, Wenbai ^{[1
]}

Li, Chunyu ^{[1
]}

Fu, Yao ^{[1
]}

Gu, Zhenhua ^{[1
]}

机构：

[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Dept Chem, 96 Jinzhai Rd, Hefei 230026, Anhui, Peoples R China

来源：

CHINESE JOURNAL OF CHEMISTRY | 2018年 / 36卷 / 01期

关键词：

palladium; visible light; C-H functionalization; isotope effect; atropisomer; PHOTOREDOX CATALYSIS; STEREOSELECTIVE-SYNTHESIS; DIARYLIODONIUM SALTS; SELECTIVE ACCESS; FUNCTIONALIZATION; ALKENES; ACTIVATION; OLEFINS; ARENES; BONDS;

D O I：

10.1002/cjoc.201700618

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A visible light accelerated C-H functionalization reaction in palladium-catalyzed arylation of vinyl arenes with diaryliodonium salts is reported in the absence of additional photosensitizer. The kinetic isotope effect (k(H)/k(D)) was changed from 3.6 (under darkness) to 1.1 when irradiated by visible light, which indicated that the C-H functionalization step was the rate determining step under darkness and significantly accelerated by the irradiation of visible light. Finally the synthesis of ortho tetra-substituted vinylarene atropisomers with high enantiospecificity was realized via this protocol.

引用

页码：11 / 14

页数：4

共 36 条

[21] Visible light-driven metal-free synthesis of highly substituted pyrroles through C-H functionalisation
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Chavant, Pierre Y.
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[27] Direct C-H arylation of 3-methoxythiophene catalyzed by Pd.: Application to a more efficient synthesis of π-alkoxy-oligothiophene derivatives
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Bechara, William S.
Constantineau-Forget, Lea
Pelletier, Guillaume
Rachel, Natalie M.
Pelletier, Joelle N.
Charette, Andre B.
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Fan, Danchen
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