Abstract
This review summarizes the interesting results obtained during the last decade in the radical aminoalkylation of a wide range of nucleophilic radicals (deriving from hydrocarbons, ethers, alcohols, halogenated derivatives and amides) promoted by transition metals. We focus on the two main procedures which recently yielded the most relevant results in this field: the dimethylzinc-air process and the new Porta reaction, based on the Ti(III)/hydroperoxide system. These protocols often provide competitive alternatives to classical landmark transformations, like the Mannich reaction and the Strecker synthesis. Moreover, a brief overview of other significant examples is given in the last section of the review.
Keywords: Imine, nucleophilic radical addition, dimethylzinc, titanium trichloride, transition metal, hydroperoxide
Mini-Reviews in Organic Chemistry
Title: Recent Developments in Nucleophilic Radical Addition to Imines: the Key Role of Transition Metals and the New Porta Radical-Type Version of the Mannich and Strecker Reactions
Volume: 6 Issue: 3
Author(s): Nadia Pastori, Cristian Gambarotti and Carlo Punta
Affiliation:
Keywords: Imine, nucleophilic radical addition, dimethylzinc, titanium trichloride, transition metal, hydroperoxide
Abstract: This review summarizes the interesting results obtained during the last decade in the radical aminoalkylation of a wide range of nucleophilic radicals (deriving from hydrocarbons, ethers, alcohols, halogenated derivatives and amides) promoted by transition metals. We focus on the two main procedures which recently yielded the most relevant results in this field: the dimethylzinc-air process and the new Porta reaction, based on the Ti(III)/hydroperoxide system. These protocols often provide competitive alternatives to classical landmark transformations, like the Mannich reaction and the Strecker synthesis. Moreover, a brief overview of other significant examples is given in the last section of the review.
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Pastori Nadia, Gambarotti Cristian and Punta Carlo, Recent Developments in Nucleophilic Radical Addition to Imines: the Key Role of Transition Metals and the New Porta Radical-Type Version of the Mannich and Strecker Reactions, Mini-Reviews in Organic Chemistry 2009; 6 (3) . https://dx.doi.org/10.2174/157019309788922702
DOI https://dx.doi.org/10.2174/157019309788922702 |
Print ISSN 1570-193X |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6298 |
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