Palladium-Catalyzed Tandem Reactions of β-(2-Bromophenyl)-α,β-Unsaturated Carbonyl Compounds with 2-Hydroxyphenylboronic Acid: A New Route to Benzo[c]chromenes

被引:9
作者
Zhu, Qihua [1 ]
Wang, Xuyan [1 ]
Xu, Yungen [1 ]
机构
[1] China Pharmaceut Univ, Dept Med Chem, Nanjing 210009, Peoples R China
关键词
Palladium; Boron; Fused-ring systems; Cross-coupling; CROSS-COUPLING REACTIONS; FORMAL RADICAL CYCLIZATION; DIRECT ARYLATION REACTIONS; GENERAL-METHOD; BENZENE RINGS; DERIVATIVES; RECEPTOR; IODIDES;
D O I
10.1002/ejoc.201101670
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Palladium-catalyzed tandem reactions of beta-(2-bromophenyl)-a,beta-unsaturated carbonyl compounds with 2-hydroxyphenylboronic acid for the synthesis of benzo[c]chromenes are presented. This mild reaction allows formation of onecarboncarbon bond and one carbonoxygen bond in one pot.
引用
收藏
页码:1112 / 1114
页数:3
相关论文
共 34 条
[1]   Control of kinetics and thermodynamics of [1,5]-shifts by aromaticity: A view through the prism of Marcus theory [J].
Alabugin, IV ;
Manoharan, M ;
Breiner, B ;
Lewis, FD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (31) :9329-9342
[2]  
[Anonymous], ORG LETT
[3]  
Barluenga J, 2002, CHEM-EUR J, V8, P2034, DOI 10.1002/1521-3765(20020503)8:9<2034::AID-CHEM2034>3.0.CO
[4]  
2-I
[5]   Catalytic direct arylation with aryl chlorides, bromides, and iodides: Intramolecular studies leading to new intermolecular reactions [J].
Campeau, LC ;
Parisien, M ;
Jean, A ;
Fagnou, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (02) :581-590
[6]   High-yielding intramolecular direct arylation reactions with aryl chlorides [J].
Campeau, LC ;
Thansandote, P ;
Fagnou, K .
ORGANIC LETTERS, 2005, 7 (09) :1857-1860
[7]   Biaryl synthesis via direct arylation: Establishment of an efficient catalyst for intramolecular processes [J].
Campeau, LC ;
Parisien, M ;
Leblanc, M ;
Fagnou, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (30) :9186-9187
[8]   Formal radical cyclization onto benzene rings:: a general method and its use in the synthesis of ent-nocardione A [J].
Clive, DLJ ;
Fletcher, SP ;
Liu, DZ .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (10) :3282-3293
[9]   Formal radical cyclization onto benzene rings -: a general method proceeding via cross-conjugated dienones [J].
Clive, DLJ ;
Fletcher, SP ;
Zhu, MZ .
CHEMICAL COMMUNICATIONS, 2003, (04) :526-527
[10]   Synthesis and characterization of non-steroidal ligands for the glucocorticoid receptor: Selective quinoline derivatives with prednisolone-equivalent functional activity [J].
Coghlan, MJ ;
Kym, PR ;
Elmore, SW ;
Wang, AX ;
Luly, JR ;
Wilcox, D ;
Stashko, M ;
Lin, CW ;
Miner, J ;
Tyree, C ;
Nakane, M ;
Jacobson, P ;
Lane, BC .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (18) :2879-2885