Palladium-catalyzed cascade reactions of 3-iodochromones with aryl iodides and norbornadiene leading to annulated xanthones

被引:46
作者
Cheng, Ming [1 ]
Yan, Jianwei [1 ]
Hu, Feng [1 ]
Chen, Hong [1 ]
Hu, Youhong [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China
基金
中国国家自然科学基金;
关键词
C-H ACTIVATION; TANDEM REACTION; 1,3-DICARBONYL COMPOUNDS; EFFICIENT APPROACH; DIRECT ARYLATION; O-TERARYLS; NORBORNENE; DERIVATIVES; CHROMONES; FUNCTIONALIZATION;
D O I
10.1039/c2sc21335d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient, palladium-catalyzed cascade reaction, which leads to formation of annulated xanthones, was devised. The process, which uses readily available 3-iodochromones, aryl iodides and norbornadiene as starting materials, takes place via a tandem Heck reaction/double C-H activation/retro-Diels-Alder pathway. The high chemoselectivity of the process is mechanistically unique and it serves as a new approach to achieve regioselective control of C-H activation in Pd/norbornene or norbornadiene systems. Its broad substrate scope, including heteroaryl coupling partners, enables access to diverse annulated xanthones.
引用
收藏
页码:526 / 530
页数:5
相关论文
共 58 条
[1]   Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[2]   PALLADIUM-CATALYZED DOMINO COUPLING REACTIONS OF ARYL HALIDES WITH NORBORNENE AND NORBORNENE DERIVATIVES - A SIMPLE ROUTE TO POLYCYCLIC AROMATIC-COMPOUNDS [J].
ALBRECHT, K ;
REISER, O ;
WEBER, M ;
KNIERIEM, B ;
DEMEIJERE, A .
TETRAHEDRON, 1994, 50 (02) :383-401
[3]   An efficient copper-catalytic system for performing intramolecular O-arylation reactions in aqueous media. New synthesis of xanthones [J].
Barbero, Nekane ;
SanMartin, Raul ;
Dominguez, Esther .
GREEN CHEMISTRY, 2009, 11 (06) :830-836
[4]   A convenient approach to the xanthone scaffold by an aqueous aromatic substitution of bromo- and iodoarenes [J].
Barbero, Nekane ;
SanMartin, Raul ;
Dominguez, Esther .
TETRAHEDRON, 2009, 65 (29-30) :5729-5732
[5]   Formal Synthesis of Nitidine and Nk109 via Palladium-Catalyzed Domino Direct Arylation/N-Arylation of Aryl Triflates [J].
Blanchot, Mathieu ;
Candito, David A. ;
Larnaud, Florent ;
Lautens, Mark .
ORGANIC LETTERS, 2011, 13 (06) :1486-1489
[6]   Palladium-Catalyzed Domino Direct Arylation/N-Arylation: Convenient Synthesis of Phenanthridines [J].
Candito, David A. ;
Lautens, Mark .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (36) :6713-6716
[7]  
Catellani M, 2005, TOP ORGANOMETAL CHEM, V14, P21
[8]   New catalytic methods for the synthesis of selectively substituted aromatics through palladacycles [J].
Catellani, M ;
Motti, E ;
Faccini, F ;
Ferraccioli, R .
PURE AND APPLIED CHEMISTRY, 2005, 77 (07) :1243-1248
[9]   Selective aryl coupling via palladacycles: a new route to m-alkylbiphenyls or m-terphenyls [J].
Catellani, M ;
Motti, E .
NEW JOURNAL OF CHEMISTRY, 1998, 22 (08) :759-761
[10]   PALLADIUM-CATALYZED SYNTHESIS OF 1,2,3,4,4A,12B-HEXAHYDRO-1,4-METHANOTRIPHENYLENES [J].
CATELLANI, M ;
CHIUSOLI, GP .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 286 (01) :C13-C16