Photosensitizer-Free, Gold-Catalyzed C-C Cross-Coupling of Boronic Acids and Diazonium Salts Enabled by Visible Light

被引：114

作者：

Witzel, Sina ^{[1
]}

Xie, Jin ^{[1
]}

Rudolph, Matthias ^{[1
]}

Hashmi, A. Stephen K. ^{[1
,2
]}

机构：

[1] Heidelberg Univ, Organ Chem Inst, Neuenheimer Feld 270, D-69120 Heidelberg, Germany

[2] King Abdulaziz Univ, Dept Chem, Fac Sci, Jeddah 21589, Saudi Arabia

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2017年 / 359卷 / 09期

关键词：

aryldiazonium salts; boronic acids; C-C coupling; gold catalysis; visible light; PHOTOREDOX CATALYSIS; ORGANOGOLD COMPOUNDS; OXIDATIVE ADDITION; ALKENES; ACTIVATION; REACTIVITY;

D O I：

10.1002/adsc.201700121

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The first photosensitizer-free visible light-driven, gold-catalyzed C-C cross-couplings of arylboronic acids and aryldiazonium salts are reported. The reactions can be conducted under very mild conditions, using a catalytic amount of tris(4-trifluoromethyl)phosphinegold(I) chloride [(4-CF3-C6H4)(3)PAuCl] with methanol as the solvent allowing an alternative access to a variety of substituted biaryls in moderate to excellent yields with broad functional group tolerance.

引用

页码：1522 / 1528

页数：7

共 50 条

[41] Copper(II)-Catalyzed C-S Cross-Coupling with Thiazolidine-2-thiones and Boronic Acids: Synthesis of Azole Sulfides [J].

Shanmugapriya, Jayabalan ;

Rajaguru, Kandasamy ;

Muthusubramanian, Shanmugam ;

Bhuvanesh, Nattamai .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (11) :1963-1967

[42] Nickel-Catalyzed Cross-Coupling of Aryl Pivalates with Cyclobutanols Involving C-O and C-C Bond Cleavage [J].

Gan, Yi ;

Zhang, Ninghui ;

Huang, Shaoxu ;

Liu, Yuanhong .

CHINESE JOURNAL OF CHEMISTRY, 2020, 38 (12) :1686-1690

[43] Synthesis of stilbene derivatives via visible-light-induced cross-coupling of aryl diazonium salts with nitroalkenes using -NO2 as a leaving group [J].

Zhang, Na ;

Quan, Zheng-Jun ;

Zhang, Zhang ;

Da, Yu-Xia ;

Wang, Xi-Cun .

CHEMICAL COMMUNICATIONS, 2016, 52 (99) :14234-14237

[44] Visible Light-Induced Photoredox and Copper-Catalyzed C-N Cross-Coupling: A Mechanistic Perspective [J].

Talekar, Sanjana S. ;

Dutta, Sayan ;

Mane, Manoj V. ;

Maity, Bholanath .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (11)

[45] Direct C-C Bond Formation through Decarboxylative Oxidative Cross-Coupling of Cinnamic Acids with Amides under Metal-Free Condition [J].

Lu, Xiaobiao ;

Xiao, Xi ;

Wan, Changfeng ;

Wang, Zhiyong ;

Liu, Jinbiao .

ACTA CHIMICA SINICA, 2021, 79 (06) :751-754

[46] Visible-Light-Induced C(sp2)―P Cross-Coupling Reactions Catalyzed by Boron Carbonitride [J].

Wang, Rong ;

Liu, Xin ;

Hou, Hao ;

Zheng, Meifang .

CHEMCATCHEM, 2025, 17 (05)

[47] Single and Twofold Metal- and Reagent-Free Anodic C-C Cross-Coupling of Phenols with Thiophenes [J].

Wiebe, Anton ;

Lips, Sebastian ;

Schollmeyer, Dieter ;

Franke, Robert ;

Waldvogel, Siegfried R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (46) :14727-14731

[48] Active Species and Mechanistic Pathways in Iron-Catalyzed C-C Bond-Forming Cross-Coupling Reactions [J].

Cassani, Carlo ;

Bergonzini, Giulia ;

Wallentin, Carl-Johan .

ACS CATALYSIS, 2016, 6 (03) :1640-1648

[49] Copper-catalyzed C-C direct cross-coupling: an efficient approach to phenyl-2-(phenylthiophenyl)-methanones [J].

Zhang, Qi ;

Wang, Wei ;

Gao, Chong ;

Cai, Rong-Rong ;

Xu, Run-Sheng .

RSC ADVANCES, 2017, 7 (33) :20123-20127

[50] Nickel-catalyzed C(sp2)-C(sp3) cross-coupling to access benzyl Bpins of arylboronic acids with α-halo boronic esters [J].

Sun, Yang ;

Zhu, Chongwei ;

Wang, Hui .

COMMUNICATIONS CHEMISTRY, 2025, 8 (01)

← 1 2 3 4 5 →