Nickel-Catalyzed Amination of Aryl Chlorides and Sulfamates in 2-Methyl-THF

被引：71

作者：

Nathel, Noah F. Fine ^{[1
]}

Kim, Junyong ^{[1
]}

Hie, Liana ^{[1
]}

Jiang, Xingyu ^{[1
]}

Garg, Neil K. ^{[1
]}

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

来源：

ACS CATALYSIS | 2014年 / 4卷 / 09期

关键词：

nickel; catalysis; amination; cross-coupling; 2-methyl-THF; green chemistry; CROSS-COUPLING REACTIONS; DIRECTED ORTHO-METALATION; IRON; MESYLATES; CLEAVAGE; COMPLEX; ETHERS;

D O I：

10.1021/cs501045v

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The nickel-catalyzed amination of aryl O-sulfamates and chlorides using the green solvent 2-methyl-THF is reported. This methodology employs the commercially available and air-stable precatalyst NiCl2(DME), is broad in scope, and provides access to aryl amines in synthetically useful yields. The utility of this methodology is underscored by examples of gram-scale couplings conducted with catalyst loadings as low as 1 mol % nickel. Moreover, the nickel-catalyzed amination described is tolerant of heterocycles and should prove useful in the synthesis of pharmaceutical candidates and other heteroatom-containing compounds. KEYWORDS: nickel, catalysis, amination, cross-coupling 2-methyl-THF, green chemistry

引用

页码：3289 / 3293

页数：5

共 65 条

[1] Palladium- and Nickel-Catalyzed Aminations of Aryl Imidazolylsulfonates and Sulfamates [J].

Ackermann, Lutz ;

Sandmann, Rene ;

Song, Weifeng .

ORGANIC LETTERS, 2011, 13 (07) :1784-1786

[2] Green chemistry tools to influence a medicinal chemistry and research chemistry based organisation [J].

Alfonsi, Kim ;

Colberg, Juan ;

Dunn, Peter J. ;

Fevig, Thomas ;

Jennings, Sandra ;

Johnson, Timothy A. ;

Kleine, H. Peter ;

Knight, Craig ;

Nagy, Mark A. ;

Perry, David A. ;

Stefaniak, Mark .

GREEN CHEMISTRY, 2008, 10 (01) :31-36

[3]

Anastas P., 1998, GREEN CHEM THEORY PR

[4] Origins, current status, and future challenges of green chemistry [J].

Anastas, PT ;

Kirchhoff, MM .

ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (09) :686-694

[5] Monodentate phosphines provide highly active catalysts for Pd-catalyzed C-N bond-forming reactions of heteroaromatic halides/amines and (H)N-heterocycles [J].

Anderson, Kevin W. ;

Tundel, Rachel E. ;

Ikawa, Takashi ;

Altman, Ryan A. ;

Buchwald, Stephen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (39) :6523-6527

[6] N,N-Diethyl O-Carbamate: Directed Metalation Group and Orthogonal Suzuki-Miyaura Cross-Coupling Partner [J].

Antoft-Finch, Aurora ;

Blackburn, Tom ;

Snieckus, Victor .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (49) :17750-17752

[7] Toxicological Assessment of 2-Methyltetrahydrofuran and Cyclopentyl Methyl Ether in Support of Their Use in Pharmaceutical Chemical Process Development [J].

Antonucci, Vincent ;

Coleman, John ;

Ferry, James B. ;

Johnson, Neil ;

Mathe, Michelle ;

Scott, Jeremy P. ;

Xu, Jing .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2011, 15 (04) :939-941

[8] Solvent applications of 2-methyltetrahydrofuran in organometallic and biphasic reactions [J].

Aycock, David F. .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2007, 11 (01) :156-159

[9] Recent Advances in Iron Catalysis in Organic Synthesis [J].

Bauer, Eike B. .

CURRENT ORGANIC CHEMISTRY, 2008, 12 (16) :1341-1369

[10] Iron-catalyzed reactions in organic synthesis [J].

Bolm, C ;

Legros, J ;

Le Paih, J ;

Zani, L .

CHEMICAL REVIEWS, 2004, 104 (12) :6217-6254

← 1 2 3 4 5 6 7 →