Synthesis of 3-Aryl-2-pyrones by Palladium-Catalyzed Cross-Coupling of Aryl Iodides with Cyclic Vinyldiazo Ester

被引:13
作者
Huang, Jun [1 ,2 ]
Li, Linyong [1 ]
Chen, Haoguo [1 ]
Xiao, Tiebo [1 ]
He, Yuwei [1 ]
Zhou, Lei [1 ]
机构
[1] Sun Yat Sen Univ, Sch Chem, 135 Xingang West Rd, Guangzhou 510275, Guangdong, Peoples R China
[2] Guangxi Teachers Educ Univ, Coll Chem & Mat Sci, 175 Mingxiu East Rd, Nanning 530001, Peoples R China
关键词
CARBENE MIGRATORY INSERTION; DIELS-ALDER REACTION; N-TOSYLHYDRAZONES; CARBON NUCLEOPHILES; DIAZO-COMPOUNDS; METAL CARBENE; 3,5-DIBROMO-2-PYRONE; 2-PYRONES; 2H-PYRAN-2-ONES; ORGANOSTANNANES;
D O I
10.1021/acs.joc.7b01470
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A palladium-catalyzed cross-coupling reaction of aryl iodides with cyclic vinyldiazo ester was developed. The reaction provides various 3-aryl-2-pyrones in good yields with high functional group tolerance. The synthetic application of the resulting 3-aryl-2-pyrones as the diene component in a Diels-Alder reaction was also described.
引用
收藏
页码:9204 / 9209
页数:6
相关论文
共 47 条
[1]   DIELS-ALDER CYCLOADDITIONS OF 2-PYRONES AND 2-PYRIDONES [J].
AFARINKIA, K ;
VINADER, V ;
NELSON, TD ;
POSNER, GH .
TETRAHEDRON, 1992, 48 (42) :9111-9171
[2]   Tosylhydrazones: New Uses for Classic Reagents in Palladium-Catalyzed Cross-Coupling and Metal-Free Reactions [J].
Barluenga, Jose ;
Valdes, Carlos .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (33) :7486-7500
[3]   Synthesis of Dienes by Palladium-Catalyzed Couplings of Tosylhydrazones with Aryl and Alkenyl Halides [J].
Barluenga, Jose ;
Tomas-Gamasa, Maria ;
Aznar, Fernando ;
Valdes, Carlos .
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (18) :3235-3240
[4]   STRUCTURE ACTIVITY STUDY OF 6-SUBSTITUTED 2-PYRANONES AS INACTIVATORS OF ALPHA-CHYMOTRYPSIN [J].
BOULANGER, WA ;
KATZENELLENBOGEN, JA .
JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (07) :1159-1163
[5]   Vinyldiazolactone as a vinylcarbene precursor: Highly selective C-H insertion and cyclopropanation reactions [J].
Bykowski, Darren ;
Wu, Kou-Hui ;
Doyle, Michael P. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (50) :16038-16039
[6]   Palladium-catalyzed reaction of allyl halides with α-diazocarbonyl compounds [J].
Chen, Shufeng ;
Wang, Jianbo .
CHEMICAL COMMUNICATIONS, 2008, (35) :4198-4200
[7]   Tandem Diels-Alder cycloadditions of 2-pyrone-5-acrylates for the efficient synthesis of novel tetracyclolactones [J].
Chung, Soo-Im ;
Seo, Joobeom ;
Cho, Cheon-Gyu .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (17) :6701-6704
[8]   Palladium-catalyzed carbene insertion and trapping with carbon nucleophiles [J].
Devine, Sean K. J. ;
Van Vranken, David L. .
ORGANIC LETTERS, 2008, 10 (10) :1909-1911
[9]   PALLADIUM-CATALYZED COUPLING OF ARYL TRIFLATES WITH ORGANOSTANNANES [J].
ECHAVARREN, AM ;
STILLE, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5478-5486
[10]   Viridepyronone, a new antifungal 6-substituted 2H-pyran-2-one produced by Trichoderma viride [J].
Evidente, A ;
Cabras, A ;
Maddau, L ;
Serra, S ;
Andolfi, A ;
Motta, A .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2003, 51 (24) :6957-6960