Rh-catalyzed sequential hydroarylation/hydrovinylation-heterocyclization of β-(2-aminophenyl)-α,β-ynones with organoboron derivatives:: A new approach to functionalized quinolines

被引：48

作者：

Abbiati, Giorgio

Arcadi, Antonio

Marinelli, Fabio

Rossi, Ellsabetta

Verdecchia, Mirella

机构：

[1] Univ Milan, Ist Chim Organ Alessandro Marchesini, I-20133 Milan, Italy

[2] Univ Aquila, Dipartimento Chim Ingn Chim & Mat, I-67010 Coppito, Italy

来源：

SYNLETT | 2006年 / 19期

关键词：

quinolines; hydroarylation; rhodium; alkynones; arylboronic acids;

D O I：

10.1055/s-2006-956462

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

4-Aryl and 4-vinyl quinolines were prepared via a sequential procedure involving regioselective Rh(acae)(C2H2)/dppf-catalyzed hydroarylation/hydrovinylation of beta-(2-aminophenyl)-alpha,beta-ynones with arylboronic acids or potassium aryl and vinyl trifluoroborates, followed by nucleophilic attack of the amino group onto the carbonyl.

引用

页码：3218 / 3224

页数：7

共 6 条

[1] Sequential alkylation/heterocyclization of β-(2-aminophenyl)-α,β-ynones promoted by electrogenerated carbanions:: A new approach to functionalized 4-alkylquinolines
Arcadi, Antonio
Bianchi, Gabriele
Inesi, Achille
Marinelli, Fabio
Rossi, Leucio
SYNLETT, 2007, (07) : 1031 - 1036
[2] The palladium-catalyzed transfer hydrogenation/heterocyclization of β-(2-aminophenyl)-α,β-ynones.: An approach to 2-aryl- and 2-vinylquinolines
Cacchi, S
Fabrizi, G
Marinelli, F
SYNLETT, 1999, (04) : 401 - 404
[3] 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
Arcadi, Antonio
Aschi, Massimiliano
Marinelli, Fabio
Verdecchia, Mirella
TETRAHEDRON, 2008, 64 (22) : 5354 - 5361
[4] A new approach to isoindolinone derivatives by sequential palladium iodide-catalyzed oxidative aminocarbonylation-heterocyclization of 2-ethynylbenzamides
Gabriele, Bartolo
Mancuso, Raffaella
Ziccarelli, Ida
Salerno, Giuseppe
TETRAHEDRON LETTERS, 2012, 53 (49) : 6694 - 6696
[5] A versatile modular approach to new chiral C2-symmetrical ferrocenyl ligands:: Highly enantioselective Rh-catalyzed hydrogenation of α-acetamidoacrylic acid derivatives
Perea, JJA
Börner, A
Knochel, P
TETRAHEDRON LETTERS, 1998, 39 (44) : 8073 - 8076
[6] Bronsted Acid Catalyzed Cascade Reactions of 2-[(2-Aminophenyl)ethynyl]phenylamine Derivatives with Aldehydes: A New Approach to the Synthesis of 2,2′-Disubstituted 1H,1′H-3,3′-Biindoles
Arcadi, Antonio
Chiarini, Marco
D'Anniballe, Gaetano
Marinelli, Fabio
Pietropaolo, Emanuela
ORGANIC LETTERS, 2014, 16 (06) : 1736 - 1739

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