Palladium-Catalyzed Cascade Reactions of 1-(3-Arylprop-2-ynyloxy)-2-bromo Benzene Derivatives with Organoboron Compounds

被引:33
作者
Arcadi, Antonio [1 ]
Blesi, Federico [1 ]
Cocchi, Sandro [2 ]
Fabrizi, Giancarlo [2 ]
Goggiamani, Antonella [2 ]
Marinelli, Fabio [1 ]
机构
[1] Univ Aquila, Dipartimento Sci Fis & Chem, I-67010 Coppito, AQ, Italy
[2] Univ Rome, Dipartimento Chim & Tecnol Farm, I-00185 Rome, Italy
关键词
SUZUKI-MIYAURA; STEREOSELECTIVE-SYNTHESIS; COUPLING REACTIONS; DOMINO REACTIONS; H ACTIVATION; CYCLIZATION; INSERTION; ACCESS; CYCLOCARBOPALLADATION; HYDROARYLATION;
D O I
10.1021/jo400503f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Applications of the cascade cyclocarbopalladation reaction followed by Suzuki-Miyaura coupling reactions of the readily available aryl-substituted propargylic aryl ethers with arylboronic acid and potassium trans-beta-styryltrifluoroborate accomplish a new versatile entry in the synthesis of benzofuran derivatives. Notably, a new approach to the challenging synthesis of C3 functionalized 2-unsubstituted benzofurans has been developed by a cyclocarbopalladation/cross-coupling/aromatization process.
引用
收藏
页码:4490 / 4498
页数:9
相关论文
共 64 条
[1]   Rh-catalyzed sequential hydroarylation/hydrovinylation-heterocyclization of β-(2-aminophenyl)-α,β-ynones with organoboron derivatives:: A new approach to functionalized quinolines [J].
Abbiati, Giorgio ;
Arcadi, Antonio ;
Marinelli, Fabio ;
Rossi, Ellsabetta ;
Verdecchia, Mirella .
SYNLETT, 2006, (19) :3218-3224
[2]   Sequential rhodium-catalyzed stereo- and regioselective addition of organoboron derivatives to the alkyl 4-hydroxy-2-alkynoates/lactonizaction reaction [J].
Alfonsi, Maria ;
Arcadi, Antonio ;
Chiarini, Marco ;
Marinelli, Fabio .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (25) :9510-9517
[3]   Gold-catalyzed synthesis of 2-substituted, 2,3-Disubstituted and 1,2,3-trisubstituted Indoles in [bmim]BF4 [J].
Ambrogio, Ilaria ;
Arcadi, Antonio ;
Cacchi, Sandro ;
Fabrizi, Giancarlo ;
Marinelli, Fabio .
SYNLETT, 2007, (11) :1775-1779
[4]  
Arcadi A., 2011, TETRAHEDRON LETT, V52, P514
[5]   Pd-catalyzed regioselective hydroarylation of α-(2-aminoaryl)-α,β-ynones with organoboron derivatives as a tool for the synthesis of quinolines:: experimental evidence and quantum-chemical calculations [J].
Arcadi, Antonio ;
Aschi, Massimiliano ;
Marinelli, Fabio ;
Verdecchia, Mirella .
TETRAHEDRON, 2008, 64 (22) :5354-5361
[6]   Multisubstituted benzo[b]furans through a copper- and/or palladium-catalyzed assembly and functionalization process [J].
Arcadi, Antonio ;
Blesi, Federico ;
Cacchi, Sandro ;
Fabrizi, Giancarlo ;
Goggiamani, Antonella ;
Marinelli, Fabio .
TETRAHEDRON, 2013, 69 (07) :1857-1871
[7]   2-Substituted 3-arylindoles through palladium-catalyzed arylative cyclization of 2-alkynyltrifluoroacetanilides with arylboronic acids under oxidative conditions [J].
Arcadi, Antonio ;
Cacchi, Sandro ;
Fabrizi, Giancarlo ;
Goggiamani, Antonella ;
Iazzetti, Antonia ;
Marinelli, Fabio .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (04) :545-548
[8]   Gold versus silver catalyzed intramolecular hydroarylation reactions of [(3-arylprop-2-ynyl)oxy]benzene derivatives [J].
Arcadi, Antonio ;
Blesi, Federico ;
Cacchi, Sandro ;
Fabrizi, Giancarlo ;
Goggiamani, Antonella ;
Marinelli, Fabio .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (48) :9700-9708
[9]   Rhodium- and Palladium-Catalyzed Hydroarylation of Propargylic Amines with Arylboronic Acids [J].
Arcadi, Antonio ;
Aschi, Massimiliano ;
Chiarini, Marco ;
Ferrara, Giovanni ;
Marinelli, Fabio .
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (2-3) :493-498
[10]   Synthetic Protocols Mutually Applicable to 4-Oxoquinolines and 4-Oxo-1,8-naphthyridines: Synthesis of 1-Aryl-2-substituted and 1-Aryl-3-fluoro-4-oxoquinolines and 4-Oxo-1,8-naphthyridines [J].
Awasaguchi, Ken-ichiro ;
Hayashi, Hiromi ;
Kawai, Hyouei ;
Tominaga, Hiroko ;
Sato, Yuichiro ;
Hayashi, Kazuya ;
Todo, Yozo .
SYNLETT, 2012, (03) :448-452