Palladium-catalyzed annulation of aryl heterocycles with strained alkenes

被引:122
作者
Hulcoop, David G. [1 ]
Lautens, Mark [1 ]
机构
[1] Univ Toronto, Dept Chem, Davenport Labs, Toronto, ON M5S 3H6, Canada
关键词
D O I
10.1021/ol070475w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An annulation reaction proceeding by the intermolecular addition of an arylpalladium(II) halide across a strained alkene, followed by an intramolecular C-H functionalization of a pendant heterocycle is described. A variety of polycyclic heterocycles have been prepared from readily accessible haloaryl heterocycles by annulation with a range of strained alkene partners.
引用
收藏
页码:1761 / 1764
页数:4
相关论文
共 26 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]   PALLADIUM-CATALYZED SYNTHESIS OF COUMARIN [J].
AN, ZW ;
CATELLANI, M ;
CHIUSOLI, GP .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 371 (03) :C51-C52
[4]   VINYLOGOUS CARBINOLAMINE TUMOR INHIBITORS .14. 1,3-DIPOLAR CYCLO-ADDITION REACTIONS WITH TETRAFLUOROBORATE AND TRIFLUOROMETHANESULFONATE SALTS OF 1,2-DIHYDROQUINOLINE AND 1,2,3,4-TETRAHYDROQUINOLINE REISSERT COMPOUNDS [J].
ANDERSON, WK ;
DERUITER, J ;
HEIDER, AR .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (05) :722-724
[5]   VYNYLOGOUS CARBINOLAMINE TUMOR INHIBITORS .23. SYNTHESIS AND ANTILEUKEMIC ACTIVITY OF BIS[[(CARBAMOYL)OXY]METHYL]-SUBSTITUTED PYRROLO[I,1-A]ISOQUINOLINES, PYRROLO[1,2-A]QUINOLINES, PYRROLO[2,1-A]ISOBENZAZEPINES, AND PYRROLO[1,2-A]BENZAZEPINES [J].
ANDERSON, WK ;
HEIDER, AR ;
RAJU, N ;
YUCHT, JA .
JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (11) :2097-2102
[6]  
[Anonymous], COMPR HETEROCYCL CHE
[7]   Carbocyclization of aromatic iodides, bicyclic alkenes, and benzynes involving a palladium-catalyzed C-H bond activation as a key step [J].
Bhuvaneswari, Sivakolundu ;
Jeganmohan, Masilamani ;
Cheng, Chien-Hong .
ORGANIC LETTERS, 2006, 8 (24) :5581-5584
[8]   Preparation of annulated nitrogen-containing heterocycles via a one-pot palladium-catalyzed alkylation/direct arylation sequence [J].
Blaszykowski, C ;
Aktoudianakis, E ;
Bressy, C ;
Alberico, D ;
Lautens, M .
ORGANIC LETTERS, 2006, 8 (10) :2043-2045
[9]   A route to annulated indoles via a palladium-catalyzed tandem alkylation/direct arylation reaction [J].
Bressy, C ;
Alberico, D ;
Lautens, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (38) :13148-13149
[10]  
CAI SX, 2004, Patent No. 2004055163