Abstract
Background and Objectives: An environmentally benign method for the activation of an alcohol is based on its temporary conversion to a more reactive carbonyl compound by transition metal-catalyzed dehydrogenation. The use of homogeneous complexes in which noble metals were recently replaced by cheap, less toxic, earth-abundant metals (Mn, Fe, Co) enabled sustainable dehydrogenative coupling reactions of alcohols and X-nucleophiles (X: C, N, O). Greener synthesis of valuable chemicals (imines, amides, esters) occurred under acceptorless conditions, while direct alkylation of amines, alcohols and carbonyl compounds was achieved through borrowing hydrogen processes. Successful applications in the preparation of pharmaceutically interesting molecules (i.e. Piribedil) are discussed. The synthetic utility was further explored in the heterocycle synthesis. Aromatic (quinolines, pyrimidines, pyrroles) and non-aromatic heterocycles (lactones, lactams, cyclic amines and imides) were built up through single or multiple C-X bond formation.
Keywords: Alcohol activation, oxidation, earth-abundant metal-complexes, acceptorless dehydrogenative coupling, borrowing hydrogen methodology, nucleophiles.
Current Organic Chemistry
Title:Synthetic Applications Based on Dehydrogenative Alcohol Activation Catalyzed by Mn-, Fe and Co-Complexes
Volume: 22 Issue: 19
Author(s): Raffaella Ferraccioli*
Affiliation:
- CNR-Istituto di Scienze e Tecnologie Molecolari (ISTM), Via C. Golgi 19, 20133 Milano,Italy
Keywords: Alcohol activation, oxidation, earth-abundant metal-complexes, acceptorless dehydrogenative coupling, borrowing hydrogen methodology, nucleophiles.
Abstract: Background and Objectives: An environmentally benign method for the activation of an alcohol is based on its temporary conversion to a more reactive carbonyl compound by transition metal-catalyzed dehydrogenation. The use of homogeneous complexes in which noble metals were recently replaced by cheap, less toxic, earth-abundant metals (Mn, Fe, Co) enabled sustainable dehydrogenative coupling reactions of alcohols and X-nucleophiles (X: C, N, O). Greener synthesis of valuable chemicals (imines, amides, esters) occurred under acceptorless conditions, while direct alkylation of amines, alcohols and carbonyl compounds was achieved through borrowing hydrogen processes. Successful applications in the preparation of pharmaceutically interesting molecules (i.e. Piribedil) are discussed. The synthetic utility was further explored in the heterocycle synthesis. Aromatic (quinolines, pyrimidines, pyrroles) and non-aromatic heterocycles (lactones, lactams, cyclic amines and imides) were built up through single or multiple C-X bond formation.
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Cite this article as:
Ferraccioli Raffaella *, Synthetic Applications Based on Dehydrogenative Alcohol Activation Catalyzed by Mn-, Fe and Co-Complexes, Current Organic Chemistry 2018; 22 (19) . https://dx.doi.org/10.2174/1385272822666180827141323
DOI https://dx.doi.org/10.2174/1385272822666180827141323 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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