Aminocarbonylation of Aryl Tosylates to Carboxamides

被引:19
作者
Chung, Seungwon [1 ]
Sach, Neal [3 ]
Choi, Chulho [1 ]
Yang, Xiaojing [1 ]
Drozda, Susan E. [1 ]
Singer, Robert A. [2 ]
Wright, Stephen W. [1 ]
机构
[1] Pfizer Global Res & Dev, Biotherapeut Chem, Groton, CT 06340 USA
[2] Pfizer Global Res & Dev, Chem Res & Dev, Groton, CT 06340 USA
[3] Pfizer Global Res & Dev, Oncol Chem, La Jolla, CA 92121 USA
关键词
PALLADIUM-CATALYZED CARBONYLATION; CROSS-COUPLING REACTIONS; ARYLBORONIC ACIDS; MESYLATES; HALIDES; ALKOXY; ALKOXYCARBONYLATION; ARENESULFONATES; CHLORIDES; PHENOLS;
D O I
10.1021/acs.orglett.5b01283
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The palladium - catalyzed aminocarbonylation of aryl tosylates with amines is reported. Suitable conditions were identified by high throughput reaction screening and then further optimized. The substrate scope of the reaction with respect to the aryl tosylate component and the amine component are reported. Competitive aminolysis of the aryl tosylates to afford the amine toluenesulfonamides and the phenol was not observed.
引用
收藏
页码:2848 / 2851
页数:4
相关论文
共 32 条
[1]   The heck reaction as a sharpening stone of palladium catalysis [J].
Beletskaya, IP ;
Cheprakov, AV .
CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066
[2]   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
[3]   PALLADIUM-CATALYZED CARBONYLATION OF ARYL TRIFLATES - SYNTHESIS OF ARENECARBOXYLIC ACID-DERIVATIVES FROM PHENOLS [J].
CACCHI, S ;
CIATTINI, PG ;
MORERA, E ;
ORTAR, G .
TETRAHEDRON LETTERS, 1986, 27 (33) :3931-3934
[4]   An efficient catalyst for Pd-catalyzed carbonylation of aryl arenesulfonates [J].
Cai, Chaoxian ;
Rivera, Nelo R. ;
Balsells, Jaume ;
Sidler, Rick R. ;
McWilliams, J. Christopher ;
Shultz, C. Scott ;
Sun, Yongkui .
ORGANIC LETTERS, 2006, 8 (22) :5161-5164
[5]   Anthraquinones related to rhein inhibit glucose uptake into chondrocytes. A mechanism for anti-osteoarthritis drugs? [J].
Carney, SL ;
Broadmore, RJ ;
Tomlinson, R ;
Kingston, A ;
Gallagher, PT ;
Owton, WM ;
Miles, MV ;
Brunavs, M ;
Smith, CW ;
Hicks, TA ;
Dobson, DR ;
Steggles, DJ ;
Ambler, SJ ;
Halliday, KA .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (07) :817-822
[6]   Ni-Catalyzed Direct Reductive Amidation via C-O Bond Cleavage [J].
Correa, Arkaitz ;
Martin, Ruben .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (20) :7253-7256
[7]   rDeveiewsign and Development of Ligands for Palladium-Catalyzed Carbonylation Reactions [J].
Fang, Weiwei ;
Zhu, Haibo ;
Deng, Qinyue ;
Liu, Shuangliang ;
Liu, Xiyu ;
Shen, Yajing ;
Tu, Tao .
SYNTHESIS-STUTTGART, 2014, 46 (13) :1689-1708
[8]   Recent developments in palladium catalysed carbonylation reactions [J].
Gadge, Sandip T. ;
Bhanage, Bhalchandra M. .
RSC ADVANCES, 2014, 4 (20) :10367-10389
[9]   SYNTHESIS OF BENZOIC AND TETRALONE CARBOXYLIC-ACID ESTERS FROM PHENOLS BY PALLADIUM CATALYZED ALKOXY ARYLOXY CARBONYLATION [J].
GERLACH, U ;
WOLLMANN, T .
TETRAHEDRON LETTERS, 1992, 33 (38) :5499-5502
[10]   Pd-catalysed carbonylations: versatile technology for discovery and process chemists [J].
Grigg, Ronald ;
Mutton, Simon P. .
TETRAHEDRON, 2010, 66 (30) :5515-5548