The Experts below are selected from a list of 6 Experts worldwide ranked by ideXlab platform
Giancarlo Fabrizi - One of the best experts on this subject based on the ideXlab platform.
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Synthesis and functionalization of indoles through palladium catalyzed reactions
Chemical Reviews, 2005Co-Authors: Sandro Cacchi, Giancarlo FabriziAbstract:The substituted indole nucleus [indole is the acronym from indigo (the natural dye) and oleum (used for the isolation)] is a structural component of a vast number of biologically active natural and unnatural compounds. The Synthesis and functionalization of indoles has been the object of research for over 100 years, and a variety of well-established classical methods are now available, to name a few of them, the Fisher indole Synthesis, the Gassman Synthesis of indoles from N-halo-anilines, the Madelung cyclization of N-acyl-o-toluidines, the Bischler indole Synthesis, the Batcho-Leimgruber Synthesis of indoles from o-nitrotoluenes and dimethylformamide acetals, and the reductive cyclization of o-nitrobenzyl ketones.1 In the last 40 years or so, however, palladiumcatalyzed reactions, generally tolerant of a wide range of functionalities and therefore applicable to complex molecules, have achieved an important place in the arsenal of the practicing organic chemist. Since the invention of an industrial process for the palladium-catalyzed production of acetaldehyde from ethylene in the presence of PdCl2 and CuCl2, an everincreasing number of organic transformations have been based on palladium catalysis. Almost every area of the organic Synthesis has been deeply influenced by the profound potential of this versatile transition metal, modifying the way organic chemists design and realize synthetic processes.2,3 Because of its catalytic nature, palladium-catalyzed Synthesis can provide access to fine chemicals, agrochemical and pharmaceutical intermediates, and active ingredients in fewer steps and with less waste than classical † In memory of Prof. Bianca Rosa Pietroni, a colleague and very close friend. * To whom correspondence should be addressed. Phone: + 39 (06) 4991-2785. Fax: + 30 (06) 4991-2780. E-mail: sandro.cacchi@ uniroma1.it. 2873 Chem. Rev. 2005, 105, 2873−2920
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the aminopalladation reductive elimination domino reaction in the construction of functionalized indole rings
European Journal of Organic Chemistry, 2002Co-Authors: Gianfranco Battistuzzi, Sandro Cacchi, Giancarlo FabriziAbstract:The aminopalladation-reductive elimination tandem reaction of internal and terminal alkynes containing proximate nitrogen nucleophiles has been proved to be a powerful and useful tool for the construction of the substituted pyrrole nucleus of the indole system. The fact that the reaction can be carried out with a wide assortment of organopalladium precursors and readily available starting alkynes, the ease of execution and the tolerance of a wide range of functional groups highlights its importance and flexibility and may contribute toward its utilization in the Synthesis of complex indole derivatives. The method may provide a versatile complement of well established classical methods such as the Batcho-Limgruber Synthesis of indoles from o-nitrotoluenes and dimethylformamide acetals, the Fisher indole Synthesis, the Gassman Synthesis of indoles from N-halo anilines, the Madelung cyclization of N-acyl-o-toluidines, and the reductive cyclization of o-nitrobenzyl ketones.
Sandro Cacchi - One of the best experts on this subject based on the ideXlab platform.
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Synthesis and functionalization of indoles through palladium catalyzed reactions
Chemical Reviews, 2005Co-Authors: Sandro Cacchi, Giancarlo FabriziAbstract:The substituted indole nucleus [indole is the acronym from indigo (the natural dye) and oleum (used for the isolation)] is a structural component of a vast number of biologically active natural and unnatural compounds. The Synthesis and functionalization of indoles has been the object of research for over 100 years, and a variety of well-established classical methods are now available, to name a few of them, the Fisher indole Synthesis, the Gassman Synthesis of indoles from N-halo-anilines, the Madelung cyclization of N-acyl-o-toluidines, the Bischler indole Synthesis, the Batcho-Leimgruber Synthesis of indoles from o-nitrotoluenes and dimethylformamide acetals, and the reductive cyclization of o-nitrobenzyl ketones.1 In the last 40 years or so, however, palladiumcatalyzed reactions, generally tolerant of a wide range of functionalities and therefore applicable to complex molecules, have achieved an important place in the arsenal of the practicing organic chemist. Since the invention of an industrial process for the palladium-catalyzed production of acetaldehyde from ethylene in the presence of PdCl2 and CuCl2, an everincreasing number of organic transformations have been based on palladium catalysis. Almost every area of the organic Synthesis has been deeply influenced by the profound potential of this versatile transition metal, modifying the way organic chemists design and realize synthetic processes.2,3 Because of its catalytic nature, palladium-catalyzed Synthesis can provide access to fine chemicals, agrochemical and pharmaceutical intermediates, and active ingredients in fewer steps and with less waste than classical † In memory of Prof. Bianca Rosa Pietroni, a colleague and very close friend. * To whom correspondence should be addressed. Phone: + 39 (06) 4991-2785. Fax: + 30 (06) 4991-2780. E-mail: sandro.cacchi@ uniroma1.it. 2873 Chem. Rev. 2005, 105, 2873−2920
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the aminopalladation reductive elimination domino reaction in the construction of functionalized indole rings
European Journal of Organic Chemistry, 2002Co-Authors: Gianfranco Battistuzzi, Sandro Cacchi, Giancarlo FabriziAbstract:The aminopalladation-reductive elimination tandem reaction of internal and terminal alkynes containing proximate nitrogen nucleophiles has been proved to be a powerful and useful tool for the construction of the substituted pyrrole nucleus of the indole system. The fact that the reaction can be carried out with a wide assortment of organopalladium precursors and readily available starting alkynes, the ease of execution and the tolerance of a wide range of functional groups highlights its importance and flexibility and may contribute toward its utilization in the Synthesis of complex indole derivatives. The method may provide a versatile complement of well established classical methods such as the Batcho-Limgruber Synthesis of indoles from o-nitrotoluenes and dimethylformamide acetals, the Fisher indole Synthesis, the Gassman Synthesis of indoles from N-halo anilines, the Madelung cyclization of N-acyl-o-toluidines, and the reductive cyclization of o-nitrobenzyl ketones.
Gianfranco Battistuzzi - One of the best experts on this subject based on the ideXlab platform.
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the aminopalladation reductive elimination domino reaction in the construction of functionalized indole rings
European Journal of Organic Chemistry, 2002Co-Authors: Gianfranco Battistuzzi, Sandro Cacchi, Giancarlo FabriziAbstract:The aminopalladation-reductive elimination tandem reaction of internal and terminal alkynes containing proximate nitrogen nucleophiles has been proved to be a powerful and useful tool for the construction of the substituted pyrrole nucleus of the indole system. The fact that the reaction can be carried out with a wide assortment of organopalladium precursors and readily available starting alkynes, the ease of execution and the tolerance of a wide range of functional groups highlights its importance and flexibility and may contribute toward its utilization in the Synthesis of complex indole derivatives. The method may provide a versatile complement of well established classical methods such as the Batcho-Limgruber Synthesis of indoles from o-nitrotoluenes and dimethylformamide acetals, the Fisher indole Synthesis, the Gassman Synthesis of indoles from N-halo anilines, the Madelung cyclization of N-acyl-o-toluidines, and the reductive cyclization of o-nitrobenzyl ketones.