Literature DB >> 18759434

A simple, cost-effective method for the regioselective deuteration of anilines.

Andrew Martins1, Mark Lautens.   

Abstract

A highly effective and operationally simple method for the regioselective deuteration of anilines is presented. A variety of electron-rich and electron-deficient anilines are efficiently deuterated at the ortho and/or para position with respect to the nitrogen in the presence of 1 equiv of conc HCl in D 2O. Under the present conditions, aromatic methoxy groups do not facilitate deuteration, enabling a chemo- and regioselective deuteration of p-anisidine.

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Year:  2008        PMID: 18759434     DOI: 10.1021/ol801763j

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  5 in total

Review 1.  Controlled microwave heating in modern organic synthesis: highlights from the 2004-2008 literature.

Authors:  C Oliver Kappe; Doris Dallinger
Journal:  Mol Divers       Date:  2009-04-21       Impact factor: 2.943

2.  Silver-catalyzed regioselective deuteration of (hetero)arenes and α-deuteration of 2-alkyl azaarenes.

Authors:  Baobiao Dong; Xuefeng Cong; Na Hao
Journal:  RSC Adv       Date:  2020-07-06       Impact factor: 3.361

3.  NHC-Stabilized Iridium Nanoparticles as Catalysts in Hydrogen Isotope Exchange Reactions of Anilines.

Authors:  Mégane Valero; Donia Bouzouita; Alberto Palazzolo; Jens Atzrodt; Christophe Dugave; Simon Tricard; Sophie Feuillastre; Grégory Pieters; Bruno Chaudret; Volker Derdau
Journal:  Angew Chem Int Ed Engl       Date:  2020-01-29       Impact factor: 15.336

4.  Manganese-Catalysed Deuterium Labelling of Anilines and Electron-Rich (Hetero)Arenes.

Authors:  Florian Bourriquen; Nils Rockstroh; Stephan Bartling; Kathrin Junge; Matthias Beller
Journal:  Angew Chem Int Ed Engl       Date:  2022-05-12       Impact factor: 16.823

5.  Palladium-Catalyzed Nondirected Late-Stage C-H Deuteration of Arenes.

Authors:  Mirxan Farizyan; Arup Mondal; Sourjya Mal; Fritz Deufel; Manuel van Gemmeren
Journal:  J Am Chem Soc       Date:  2021-09-28       Impact factor: 15.419

  5 in total

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