Photoinduced oxidative activation of electron-rich arenes: alkenylation with H2 evolution under external oxidant-free conditions

被引：60

作者：

Hu, Xia ^{[1
]}

Zhang, Guoting ^{[1
]}

Bu, Faxiang ^{[1
]}

Luo, Xu ^{[1
]}

Yi, Kebing ^{[1
]}

Zhang, Heng ^{[1
]}

Lei, Aiwen ^{[1
,2
,3
]}

机构：

[1] Wuhan Univ, Coll Chem & Mol Sci, IAS, Wuhan 430072, Hubei, Peoples R China

[2] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China

[3] Nankai Univ, Inst Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

CHEMICAL SCIENCE | 2018年 / 9卷 / 06期

基金：

中国国家自然科学基金;

关键词：

LIGHT PHOTOREDOX CATALYSIS; C-H AMINATION; VISIBLE-LIGHT; RADICAL CATIONS; AROMATIC-COMPOUNDS; ORGANIC-SYNTHESIS; ROOM-TEMPERATURE; FUNCTIONALIZATION; OLEFINATION; ARYL;

D O I：

10.1039/c7sc04634k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The dehydrogenative cross- coupling of arenes and alkenes is a particularly ideal approach for the synthesis of aryl alkenes. Herein, we report a photo- induced C-H/C-H cross- coupling between electron- rich arenes and styrene derivatives using a dual catalytic system containing an acridinium photosensitizer and a cobaloxime proton- reducing catalyst. This catalytic system enables the Csp(2)-Csp(2) bond formation accompanying H-2 evolution. Various substituted aryl alkenes can be afforded with good to excellent yields and high beta-regioselectivity.

引用

页码：1521 / 1526

页数：6

共 23 条

[1] A low-cost electrochemical thio- and selenocyanation strategy for electron-rich arenes under catalyst- and oxidant-free conditions
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[4] Palladium-Catalyzed Alkenylation of Quinoline-N-oxides via C-H Activation under External-Oxidant-Free Conditions
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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (39) : 13888 - +
[5] Visible-Light-Induced External Oxidant-Free Oxidative Phosphonylation of C(sp2)-H Bonds
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Liu, Jiamei
Yi, Hong
Wang, Shengchun
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[6] Oxidative monobromination of electron-rich arenes by conc. H2SO4/alkali metal bromides
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[7] Visible light-mediated oxidative C(sp3)-H phosphonylation for α-aminophosphonates under oxidant-free conditions
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Wang, Shengchun
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[8] Selective Cyclization of Arylnitrones to Indolines under External Oxidant-Free Conditions: Dual Role of Rh(III) Catalyst in the C-H Activation and Oxygen Atom Transfer
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[9] Oxidative [4+2] annulation of styrenes with alkynes under external-oxidant-free conditions
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[10] Oxidative [4+2] annulation of styrenes with alkynes under external-oxidant-free conditions
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