Recent advances in heterobimetallic palladium(II)/copper(II) catalyzed domino difunctionalization of carbon-carbon multiple bonds

被引:83
作者
Beccalli, Egle M. [1 ]
Broggini, Gianluigi [2 ]
Gazzola, Silvia [2 ]
Mazza, Alberto [1 ]
机构
[1] DISFARM, Sez Chim Gen Organ A Marchesini, I-20133 Milan, Italy
[2] Univ Insubria, Dipartimento Sci & Alta Tecnol, I-22100 Como, Italy
关键词
C-H ACTIVATION; INTRAMOLECULAR DIAMINATION; PD(II)-CATALYZED CYCLIZATION; STEREOSELECTIVE-SYNTHESIS; STRAIGHTFORWARD SYNTHESIS; EFFICIENT SYNTHESIS; ALLYLIC ALCOHOLS; VINYL ETHERS; C-6; HOMOLOGS; PALLADIUM;
D O I
10.1039/c4ob00610k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The double functionalization of carbon-carbon multiple bonds in one-pot processes has emerged in recent years as a fruitful tool for the rapid synthesis of complex molecular scaffolds. This review covers the advances in domino reactions promoted by the couple palladium(II)/copper(II), which was proven to be an excellent catalytic system for the functionalization of substrates.
引用
收藏
页码:6767 / 6789
页数:23
相关论文
共 117 条
[11]   Pd(II)-catalyzed conversion of styrene derivatives to acetals: Impact of (-)-sparteine on regioselectivity [J].
Balija, AM ;
Stowers, KJ ;
Schultz, MJ ;
Sigman, MS .
ORGANIC LETTERS, 2006, 8 (06) :1121-1124
[12]   O-alkenyl hydroxylamines:: A new concept for cyclofunctionalization [J].
Bates, RW ;
Sa-Ei, K .
ORGANIC LETTERS, 2002, 4 (24) :4225-4227
[13]   Intramolecular Pd(II)-catalyzed cyclization of propargylamides: Straightforward synthesis of 5-oxazolecarbaldehydes [J].
Beccalli, Egle M. ;
Borsini, Elena ;
Broggini, Gianluigi ;
Palmisano, Giovanni ;
Sottocornola, Silvia .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (12) :4746-4749
[14]   Intramolecular palladium-catalyzed oxidative coupling on thiophene and furan rings: Determinant role of the electronic availability of the heterocycle [J].
Beccalli, Egle M. ;
Borsini, Elena ;
Broggini, Gianluigi ;
Rigamonti, Micol ;
Sottocornola, Silvia .
SYNLETT, 2008, (07) :1053-1057
[15]   C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents [J].
Beccalli, Egle M. ;
Broggini, Gianluigi ;
Martinelli, Michela ;
Sottocornola, Silvia .
CHEMICAL REVIEWS, 2007, 107 (11) :5318-5365
[16]   Palladium- and copper-mediated direct C-2 arylation of azoles - Including free (NH)-imidazole, -benzimidazole and -indole - Under base-free and ligandless conditions [J].
Bellina, F ;
Cauteruccio, S ;
Rossi, R .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (06) :1379-1382
[17]   Ligandless microwave-assisted Pd/Cu-catalyzed direct arylation of oxazoles [J].
Besselievre, Francois ;
Mahuteau-Betzer, Florence ;
Grierson, David S. ;
Piguel, Sandrine .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (08) :3278-3280
[18]   Intramolecular Palladium-Catalyzed Aminocarboxylation of Olefins as a Direct Route to Bicyclic Oxazolidinones [J].
Borsini, Elena ;
Broggini, Gianluigi ;
Fasana, Andrea ;
Galli, Simona ;
Khansaa, Maisaa ;
Piarulli, Umberto ;
Rigamonti, Micol .
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (06) :985-994
[19]   Enantiopure 2-piperidylacetaldehyde as a useful building block in the diversity-oriented synthesis of polycyclic piperidine derivatives [J].
Borsini, Elena ;
Broggini, Gianluigi ;
Colombo, Francesco ;
Khansaa, Maisaa ;
Fasana, Andrea ;
Galli, Simona ;
Passarella, Daniele ;
Riva, Elena ;
Riva, Sergio .
TETRAHEDRON-ASYMMETRY, 2011, 22 (03) :264-269
[20]   Selective Intramolecular Palladium(II)-Catalyzed Aminooxygenation vs. Diamination of Alkenylureas: Efficient Microwave-Assisted Reactions to Bicyclic Piperazinones [J].
Broggini, Gianluigi ;
Barbera, Vincenzina ;
Beccalli, Egle M. ;
Chiacchio, Ugo ;
Fasana, Andrea ;
Galli, Simona ;
Gazzola, Silvia .
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (08) :1640-1648