Decarboxylative Aminomethylation of Aryl- and Vinylsulfonates through Combined Nickel- and Photoredox-Catalyzed Cross-Coupling

被引：85

作者：

Fan, Lulu ^{[1
]}

Jia, Jiaqi ^{[1
]}

Hou, Hong ^{[1
]}

Lefebvre, Quentin ^{[1
]}

Rueping, Magnus ^{[1
,2
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, Landoltweg 1, D-52074 Aachen, Germany

[2] KAUST, KAUST Catalysis Ctr KCC, Thuwal 239556900, Saudi Arabia

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 46期

基金：

欧洲研究理事会;

关键词：

amino acids; cross-coupling; decarboxylation; nickel catalysis; photoredox catalysis; SINGLE-ELECTRON TRANSMETALATION; VISIBLE-LIGHT PHOTOCATALYSIS; O BOND ACTIVATION; C-H BONDS; DUAL CATALYSIS; MERGING PHOTOREDOX; PHENOL DERIVATIVES; ORGANIC-SYNTHESIS; CARBOXYLIC-ACIDS; METAL CATALYSIS;

D O I：

10.1002/chem.201604452

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A mild approach for the decarboxylative aminomethylation of aryl sulfonates by the combination of photoredox and nickel catalysis through C-O bond cleavage is described for the first time. A wide range of aryl triflates as well as aryl mesylates, tosylates and alkenyl triflates afford the corresponding products in good to excellent yields.

引用

页码：16437 / 16440

页数：4

共 73 条

[41] Merging Photoredox and Nickel Catalysis: Decarboxylative Cross-Coupling of Carboxylic Acids with Vinyl Halides [J].

Noble, Adam ;

McCarver, Stefan J. ;

MacMillan, David W. C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (02) :624-627

[42] Photoredox Mediated Nickel Catalyzed Cross-Coupling of Thiols With Aryl and Heteroaryl Iodides via Thiyl Radicals [J].

Oderinde, Martins S. ;

Frenette, Mathieu ;

Robbins, Daniel W. ;

Aquila, Brian ;

Johannes, Jeffrey W. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (06) :1760-1763

[43] Phenol Derivatives as Coupling Partners with Alkylsilicates in Photoredox/Nickel Dual Catalysis [J].

Patel, Niki R. ;

Molander, Gary A. .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (16) :7271-7275

[44] Engaging Alkenyl Halides with Alkylsilicates via Photoredox Dual Catalysis [J].

Patel, Niki R. ;

Kelly, Christopher B. ;

Jouffroy, Matthieu ;

Molander, Gary A. .

ORGANIC LETTERS, 2016, 18 (04) :764-767

[45] Nickel-catalysed Negishi cross-coupling reactions: scope and mechanisms [J].

Phapale, Vilas B. ;

Cardenas, Diego J. .

CHEMICAL SOCIETY REVIEWS, 2009, 38 (06) :1598-1607

[46] Visible Light Photoredox Catalysis with Transition Metal Complexes: Applications in Organic Synthesis [J].

Prier, Christopher K. ;

Rankic, Danica A. ;

MacMillan, David W. C. .

CHEMICAL REVIEWS, 2013, 113 (07) :5322-5363

[47] Single-Electron Transmetalation: An Enabling Technology for Secondary Alkylboron Cross-Coupling [J].

Primer, David N. ;

Karakaya, Idris ;

Tellis, John C. ;

Molander, Gary A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (06) :2195-2198

[48] Dyes as Visible Light Photoredox Organocatalysts [J].

Ravelli, Davide ;

Fagnoni, Maurizio .

CHEMCATCHEM, 2012, 4 (02) :169-171

[49] Nickel-Catalyzed Cross-Couplings Involving Carbon-Oxygen Bonds [J].

Rosen, Brad M. ;

Quasdorf, Kyle W. ;

Wilson, Daniella A. ;

Zhang, Na ;

Resmerita, Ana-Maria ;

Garg, Neil K. ;

Percec, Virgil .

CHEMICAL REVIEWS, 2011, 111 (03) :1346-1416

[50] Single-Electron Transmetalation: Synthesis of 1,1-Diaryl-2,2,2-trifluoroethanes by Photoredox/Nickel Dual Catalytic Cross-Coupling [J].

Ryu, DaWeon ;

Primer, David N. ;

Tellis, John C. ;

Molander, Gary A. .

CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (01) :120-123

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