Literature DB >> 16620104

Free-radical version of the strecker synthesis of alpha-aminoamides promoted by aqueous H2O2/TiCl3/HCONH2 system.

Rosalba Cannella1, Angelo Clerici, Walter Panzeri, Nadia Pastori, Carlo Punta, Ombretta Porta.   

Abstract

A new reaction of general synthetic interest representing the free-radical version of the Strecker synthesis to alpha-aminoamides is reported. A hydroxy radical, generated by Ti(III) one-electron reduction of H2O2, abstracts a H atom from the C-H bond of formamide, and the resulting carbamoyl radical adds to the C atom of aldimines formed in situ, leading to a one-pot synthesis of alpha-aminoamides. Several types of aldehydes can participate in this process.

Entities:  

Year:  2006        PMID: 16620104     DOI: 10.1021/ja061092g

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  3 in total

1.  Titanium Radical Redox Catalysis: Recent Innovations in Catalysts, Reactions, and Modes of Activation.

Authors:  Xiangyu Wu; Yejin Chang; Song Lin
Journal:  Chem       Date:  2022-07-01       Impact factor: 25.832

2.  Multicomponent versus domino reactions: One-pot free-radical synthesis of β-amino-ethers and β-amino-alcohols.

Authors:  Bianca Rossi; Nadia Pastori; Simona Prosperini; Carlo Punta
Journal:  Beilstein J Org Chem       Date:  2015-01-15       Impact factor: 2.883

Review 3.  New advances in titanium-mediated free radical reactions.

Authors:  Bianca Rossi; Simona Prosperini; Nadia Pastori; Angelo Clerici; Carlo Punta
Journal:  Molecules       Date:  2012-12-11       Impact factor: 4.411

  3 in total

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