Ni-Catalyzed Direct Reductive Amidation via C-O Bond Cleavage

被引:131
作者
Correa, Arkaitz [1 ]
Martin, Ruben [1 ,2 ]
机构
[1] Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain
[2] Catalan Inst Res & Adv Studies ICREA, Barcelona 08010, Spain
基金
欧洲研究理事会;
关键词
UNACTIVATED ALKYL BROMIDES; CROSS-COUPLING REACTIONS; ARYL HALIDES; DIRECT CARBOXYLATION; OXIDATIVE AMIDATION; BENZYL HALIDES; ISOCYANATES; ALDEHYDES; ELECTROPHILES; REACTIVITY;
D O I
10.1021/ja5029793
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel Ni-catalyzed reductive amidation of C(sp(2))-O and C(sp(3))-O electrophiles with isocyanates is described. This umpolung reaction allows for an unconventional preparation of benzamides using simple starting materials and easy-to-handle Ni catalysts.
引用
收藏
页码:7253 / 7256
页数:4
相关论文
共 81 条
[1]   Ni-Catalyzed Reduction of Inert C-O Bonds: A New Strategy for Using Aryl Ethers as Easily Removable Directing Groups [J].
Alvarez-Bercedo, Paula ;
Martin, Ruben .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (49) :17352-17353
[2]   Decarbonylative C-H Coupling of Azoles and Aryl Esters: Unprecedented Nickel Catalysis and Application to the Synthesis of Muscoride A [J].
Amaike, Kazuma ;
Muto, Kei ;
Yamaguchi, Junichiro ;
Itami, Kenichiro .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) :13573-13576
[3]   Selective Cross-Coupling of Organic Halides with Allylic Acetates [J].
Anka-Lufford, Lukiana L. ;
Prinsell, Michael R. ;
Weix, Daniel J. .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (22) :9989-10000
[4]  
[Anonymous], 2013, ACS CATA L
[5]  
Arthur G., 2000, The Amide Linkage: Selected Structural Aspects in Chemistry, Biochemistry, and Materials Science
[6]   BONDING OF AROMATIC-HYDROCARBONS TO NI(O) - STRUCTURE OF BISTRICYCLOHEXYLPHOSPHINE(1,2-ETA-2-ANTHRACENE)NICKEL(O)-TOLUENE [J].
BRAUER, DJ ;
KRUGER, C .
INORGANIC CHEMISTRY, 1977, 16 (04) :884-891
[7]   Palladium-Catalyzed Carbonylation Reactions of Aryl Halides and Related Compounds [J].
Brennfuehrer, Anne ;
Neumann, Helfried ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (23) :4114-4133
[8]   DIRECTING EFFECTS IN INORGANIC SUBSTITUTION REACTIONS .1. A HYPOTHESIS TO EXPLAIN THE TRANS-EFFECT [J].
CHATT, J ;
DUNCANSON, LA ;
VENANZI, LM .
JOURNAL OF THE CHEMICAL SOCIETY, 1955, :4456-4460
[9]   Catalytic Asymmetric Reductive Acyl Cross-Coupling: Synthesis of Enantioenriched Acyclic α,α-Disubstituted Ketones [J].
Cherney, Alan H. ;
Kadunce, Nathaniel T. ;
Reisman, Sarah E. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (20) :7442-7445
[10]   Diverse functionalization of thiazolo ring-fused 2-pyridones [J].
Chorell, Erik ;
Das, Pralay ;
Almqvist, Fredrik .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (13) :4917-4924