Palladium(II)/Copper Halide/Solvent Combination for Selective Intramolecular Domino Reactions of Indolecarboxylic Acid Allylamides: An Unprecedented Arylation/Esterification Sequence
作者： Gianluigi Broggini , Vincenzina Barbera , Egle M Beccalli , Elena Borsini , Simona Galli
关键词:
摘要: Intramolecular oxidative palladium-catalyzed reactions of indolylallylamides in the presence couple bis(acetonitrile) palladium dichloride and copper(II) halide are described. Starting from 2- 3-indolylallylamides involving both cases C-3 position indole nucleus, variously substituted β-carbolinones were obtained by arylation/halogenation, arylation/esterification or arylation/carboalkoxylation processes. On other hand, an unusual aminohalogenation/halogenation sequence performed on 2-indolylallylamides gave rise to pyrazino[1,2-a]indole products. The carboesterification process is result unknown path that involves DMF DMA used as solvent. outcome arises a totally selective 1,2-migration acyl group supposed spiro intermediates formed nucleophilic attack position.
core.ac.uk
sci-hub.se 参考文章(98)
�va Balogh-Hergovich, G�bor Speier, The chlorination of indoles by copper(II) chloride Journal of The Chemical Society-perkin Transactions 1. pp. 2305- 2308 ,(1986) , 10.1039/P19860002305
Huanfeng Jiang, Shengming Ma, Guoxin Zhu, Xiyan Lu, Structural factors affecting the selectivities in the palladium (II) catalyzed cyclization of N-alkenyl-2-alkynamides Tetrahedron. ,vol. 52, pp. 10945- 10954 ,(1996) , 10.1016/0040-4020(96)00648-5
Allison R. Dick, Matthew S. Remy, Jeff W. Kampf, Melanie S. Sanford, Carbon−Nitrogen Bond-Forming Reactions of Palladacycles with Hypervalent Iodine Reagents Organometallics. ,vol. 26, pp. 1365- 1370 ,(2007) , 10.1021/OM061052L
Luca Basolo, Egle M. Beccalli, Elena Borsini, Gianluigi Broggini, Efficient palladium-catalyzed direct arylation of azines and diazines using ligand-free conditions Tetrahedron. ,vol. 65, pp. 3486- 3491 ,(2009) , 10.1016/J.TET.2009.02.025
Gnuni Karapetyan, Kuheli Chakrabarty, Martin Hein, Peter Langer, Synthesis and bioactivity of carbohydrate derivatives of indigo, its isomers and heteroanalogues. ChemMedChem. ,vol. 6, pp. 25- 37 ,(2011) , 10.1002/CMDC.201000374
Jing-Mei Huang, Yi Dong, Xu-Xiao Wang, Hui-Chao Luo, Highly regio- and stereoselective intermolecular tandem reaction to synthesize chloro-substituted 1,3-butadienes Chemical Communications. ,vol. 46, pp. 1035- 1037 ,(2010) , 10.1039/B923464K
Grégory L. J. Bar, Guy C. Lloyd-Jones, Kevin I. Booker-Milburn, Pd(II)-Catalyzed Intermolecular 1,2-Diamination of Conjugated Dienes Journal of the American Chemical Society. ,vol. 127, pp. 7308- 7309 ,(2005) , 10.1021/JA051181D
Giuseppe Bartoli, Giorgio Bencivenni, Renato Dalpozzo, Organocatalytic strategies for the asymmetric functionalization of indoles Chemical Society Reviews. ,vol. 39, pp. 4449- 4465 ,(2010) , 10.1039/B923063G
Marco Bandini, Astrid Eichholzer, Catalytic Functionalization of Indoles in a New Dimension Angewandte Chemie. ,vol. 48, pp. 9608- 9644 ,(2009) , 10.1002/ANIE.200901843
Shengming Ma, Bin Wu, Shimin Zhao, Mild and efficient synthesis of (Z)-α-chloroakylidene-β-lactones via the PdCl^2-catalyzed cyclocarbonylation of 2-alkynols Organic Letters. ,vol. 5, pp. 4429- 4432 ,(2003) , 10.1021/OL0357245