Palladium-catalyzed β-(hetero)arylation of α,β-unsaturated valerolactams

被引:11
作者
Canterbury, Daniel P. [1 ]
Hesp, Kevin D. [1 ]
Polivkova, Jana [1 ]
机构
[1] Pfizer Worldwide Med Chem, Eastern Point Rd, Groton, CT 06340 USA
关键词
MILD CONDITIONS; ARYL CHLORIDES; HECK REACTION; COUPLING REACTIONS; LACTAMS; ACID; ARYLATION; ALKENES; OLEFINS; SCOPE;
D O I
10.1039/c6ob01126h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A method for the palladium-catalyzed arylation of alpha,beta-unsaturated valerolactams is reported. This new protocol provides arylation products in yields up to 95% and is applicable to a wide array of aryl and heteroaryl bromides. The optimization, scope and limitations are described.
引用
收藏
页码:7731 / 7734
页数:4
相关论文
共 32 条
[1]   Unprecedented oxidation of a phenylglycinol-derived 2-pyridone: Enantioselective synthesis of polyhydroxypiperidines [J].
Amat, M ;
Llor, N ;
Huguet, M ;
Molins, E ;
Espinosa, E ;
Bosch, J .
ORGANIC LETTERS, 2001, 3 (21) :3257-3260
[2]  
Amgen Inc., 2011, [No title captured], Patent No. [WO2011143129A1, 2011143129, WO2011143129]
[3]   Highly Enantioselective Catalytic Synthesis of Neurite Growth-Promoting Secoyohimbanes [J].
Antonchick, Andrey P. ;
Lopez-Tosco, Sara ;
Parga, Juan ;
Sievers, Sonja ;
Schuermann, Markus ;
Preut, Hans ;
Hoeing, Susanne ;
Schoeler, Hans R. ;
Sterneckert, Jared ;
Rauh, Daniel ;
Waldmann, Herbert .
CHEMISTRY & BIOLOGY, 2013, 20 (04) :500-509
[4]  
Bagdanoff, 2015, Patent No. [WO2015066188A1, 2015066188]
[5]   The heck reaction as a sharpening stone of palladium catalysis [J].
Beletskaya, IP ;
Cheprakov, AV .
CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066
[6]   RECENT DEVELOPMENTS AND NEW PERSPECTIVES IN THE HECK REACTION [J].
CABRI, W ;
CANDIANI, I .
ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (01) :2-7
[7]   Ring-closing metathesis for the synthesis of heteroaromatics: evaluating routes to pyridines and pyridazines [J].
Donohoe, Timothy J. ;
Bower, John F. ;
Basutto, Jose A. ;
Fishlock, Lisa P. ;
Procopiou, Panayiotis A. ;
Callens, Cedric K. A. .
TETRAHEDRON, 2009, 65 (44) :8969-8980
[8]   Recent advances in the Heck-Matsuda reaction in heterocyclic chemistry [J].
Felpin, Francois-Xavier ;
Nassar-Hardy, Luma ;
Le Callonnec, Francois ;
Fouquet, Eric .
TETRAHEDRON, 2011, 67 (16) :2815-2831
[9]   Efficient Suzuki-Miyaura coupling of (hetero)aryl chlorides with thiophene- and furanboronic acids in aqueous n-butanol [J].
Fleckenstein, Christoph A. ;
Plenio, Herbert .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (08) :3236-3244
[10]   Organometallic enantiomeric scaffolding:: General access to 2-substituted oxa- and azabicyclo[3.2.1]octenes via a bronsted acid catalyzed [5+2] cycloaddition reaction [J].
Garnier, Ethel C. ;
Liebeskind, Lanny S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (23) :7449-7458