Literature DB >> 25223494

Sustainable three-component synthesis of isothioureas from isocyanides, thiosulfonates, and amines.

Pieter Mampuys1, Yanping Zhu, Tjøstil Vlaar, Eelco Ruijter, Romano V A Orru, Bert U W Maes.   

Abstract

Multiple applications of isothioureas as fine chemicals (or their precursors) are known, but a general sustainable method for their synthesis was hitherto unavailable. We report a novel general approach towards S-alkyl and S-aryl isothioureas through a copper(I)-catalyzed three-component reaction between amines, isocyanides, and thiosulfonates. The formal synthesis of a superpotent sweetener further illustrates the applicability of our method.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Lewis acids; copper catalysis; isocyanides; isothioureas; molecular sieves

Mesh:

Substances:

Year:  2014        PMID: 25223494     DOI: 10.1002/anie.201406717

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  4 in total

Review 1.  α-Aminoazoles/azines: key reaction partners for multicomponent reactions.

Authors:  Shah Imtiaz; Jahangir Ahmad War; Syqa Banoo; Sarfaraz Khan
Journal:  RSC Adv       Date:  2021-03-16       Impact factor: 3.361

2.  Nickel-catalyzed reductive thiolation and selenylation of unactivated alkyl bromides.

Authors:  Yi Fang; Torben Rogge; Lutz Ackermann; Shun-Yi Wang; Shun-Jun Ji
Journal:  Nat Commun       Date:  2018-06-08       Impact factor: 14.919

3.  Direct synthesis of 2-oxo-acetamidines from methyl ketones, aromatic amines and DMF via copper-catalyzed C(sp3)-H amidination.

Authors:  Dianke Xie; Wei He; Jiang Xiao; Yao Wu; Yongjia Guo; Qiang Liu; Cancheng Guo
Journal:  RSC Adv       Date:  2019-03-04       Impact factor: 4.036

4.  A straightforward and convenient synthesis of functionalized allyl thiosulfonates and allyl disulfanes.

Authors:  Raju Jannapu Reddy; Md Waheed; Jangam Jagadesh Kumar
Journal:  RSC Adv       Date:  2018-12-04       Impact factor: 4.036

  4 in total

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