Copper-Catalyzed Double C-S Bonds Formation via Different Paths: Synthesis of Benzothiazoles from N-Benzyl-2-iodoaniline and Potassium Sulfide

被引:118
作者
Zhang, Xiaoyun [1 ]
Zeng, Weilan [1 ]
Yang, Yuan [1 ]
Huang, Hui [1 ]
Liang, Yun [1 ,2 ]
机构
[1] Hunan Normal Univ, Chem Biol & Tradit Chinese Med Res, Natl & Local Joint Engn Lab New Petrochem Mat & F, Minist Educ, Changsha 410081, Hunan, Peoples R China
[2] Beijing Natl Lab Mol Sci, Beijing 100871, Peoples R China
关键词
HIGHLY EFFICIENT METHOD; ONE-POT SYNTHESIS; CARBON-SULFUR; ARYL HALIDES; SUBSTITUTED BENZOTHIAZOLES; COUPLING REACTIONS; 3-COMPONENT SYNTHESIS; PARALLEL SYNTHESIS; H BOND; THIOLS;
D O I
10.1021/ol403638d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new, highly efficient procedure for the synthesis of benzothiazoles from easily available N-benzyl-2-iodoaniline and potassium sulfide has been developed. The results show copper-catalyzed double C-S bond formation via a traditional cross-coupling reaction and an oxidative cross-coupling reaction.
引用
收藏
页码:876 / 879
页数:4
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[1]   Synthesis and biological properties of benzothiazole, benzoxazole, and chromen-4-one analogues of the potent antitumor agent 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole (PMX 610, NSC 721648) [J].
Aiello, Stefania ;
Wells, Geoffrey ;
Stone, Erica L. ;
Kadri, Hachemi ;
Bazzi, Rana ;
Bell, David R. ;
Stevens, Malcolm F. G. ;
Matthews, Charles S. ;
Bradshaw, Tracey D. ;
Westwell, Andrew D. .
JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (16) :5135-5139
[2]   Aerobic Copper-Catalyzed Organic Reactions [J].
Allen, Scott E. ;
Walvoord, Ryan R. ;
Padilla-Salinas, Rosaura ;
Kozlowski, Marisa C. .
CHEMICAL REVIEWS, 2013, 113 (08) :6234-6458
[3]   Resting State and Elementary Steps of the Coupling of Aryl Halides with Thiols Catalyzed by Alkylbisphosphine Complexes of Palladium [J].
Alvaro, Elsa ;
Hartwig, John F. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (22) :7858-7868
[4]   Rhodium-catalyzed substitution reaction of aryl fluorides with disulfides:: p-orientation in the polyarylthiolation of polyfluorobenzenes [J].
Arisawa, Mieko ;
Suzuki, Takaaki ;
Ishikawa, Tomofumi ;
Yamaguchi, Masahiko .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (37) :12214-+
[5]   Rhodium-Catalyzed Synthesis of Diaryl Sulfides Using Aryl Fluorides and Sulfur/Organopolysulfides [J].
Arisawa, Mieko ;
Ichikawa, Takuya ;
Yamaguchi, Masahiko .
ORGANIC LETTERS, 2012, 14 (20) :5318-5321
[6]   Mild and highly efficient method for the synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazoles [J].
Bahrami, Kiumars ;
Khodaei, M. Mehdi ;
Naali, Fardin .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (17) :6835-6837
[7]   Copper-catalyzed synthesis of vinyl sulfides [J].
Bates, CG ;
Saejueng, P ;
Doherty, MQ ;
Venkataraman, D .
ORGANIC LETTERS, 2004, 6 (26) :5005-5008
[8]   A general method for the formation of aryl-sulfur bonds using copper(I) catalysts [J].
Bates, CG ;
Gujadhur, RK ;
Venkataraman, D .
ORGANIC LETTERS, 2002, 4 (16) :2803-2806
[9]   Transition-Metal-Catalyzed C-S, C-Se, and C-Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions [J].
Beletskaya, Irina P. ;
Ananikov, Valentine P. .
CHEMICAL REVIEWS, 2011, 111 (03) :1596-1636
[10]   A Comparative Mechanistic Study of Cu-Catalyzed Oxidative Coupling Reactions with N-Phenyltetrahydroisoquinoline [J].
Boess, Esther ;
Schmitz, Corinna ;
Klussmann, Martin .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (11) :5317-5325