Literature DB >> 24719367

Light-induced ruthenium-catalyzed nitrene transfer reactions: a photochemical approach towards N-acyl sulfimides and sulfoximines.

Vincent Bizet1, Laura Buglioni, Carsten Bolm.   

Abstract

1,4,2-Dioxazol-5-ones are five-membered heterocycles known to decarboxylate under thermal or photochemical conditions, thus yielding N-acyl nitrenes. Described herein is a light-induced ruthenium-catalyzed N-acyl nitrene transfer to sulfides and sulfoxides by decarboxylation of 1,4,2-dioxazol-5-ones at room temperature, thus providing direct access to N-acyl sulfimides and sulfoximines under mild reaction conditions. In addition, a one-pot sulfur imidation/oxidation sequence catalyzed by a single ruthenium complex is reported.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  homogeneous catalysis; nitrenes; photochemistry; ruthenium; synthetic methods

Year:  2014        PMID: 24719367     DOI: 10.1002/anie.201310790

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


  13 in total

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Journal:  J Org Chem       Date:  2018-06-27       Impact factor: 4.354

4.  Visible-Light-Induced Decarboxylation of Dioxazolones to Phosphinimidic Amides and Ureas.

Authors:  Jie Pan; Haocong Li; Kai Sun; Shi Tang; Bing Yu
Journal:  Molecules       Date:  2022-06-07       Impact factor: 4.927

5.  Synthesis of Chiral Tetrasubstituted Azetidines from Donor-Acceptor Azetines via Asymmetric Copper(I)-Catalyzed Imido-Ylide [3+1]-Cycloaddition with Metallo-Enolcarbenes.

Authors:  Kostiantyn O Marichev; Kan Wang; Kuiyong Dong; Nicole Greco; Lynée A Massey; Yongming Deng; Hadi Arman; Michael P Doyle
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-24       Impact factor: 15.336

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Journal:  Chem Sci       Date:  2018-04-30       Impact factor: 9.825

7.  Efficient Copper-Catalyzed Multicomponent Synthesis of N-Acyl Amidines via Acyl Nitrenes.

Authors:  Kaj M van Vliet; Lara H Polak; Maxime A Siegler; Jarl Ivar van der Vlugt; Célia Fonseca Guerra; Bas de Bruin
Journal:  J Am Chem Soc       Date:  2019-09-10       Impact factor: 15.419

8.  Novel Broccoli Sulforaphane-Based Analogues Inhibit the Progression of Pancreatic Cancer without Side Effects.

Authors:  Christina Georgikou; Laura Buglioni; Maximilian Bremerich; Nico Roubicek; Libo Yin; Wolfgang Gross; Carsten Sticht; Carsten Bolm; Ingrid Herr
Journal:  Biomolecules       Date:  2020-05-15

9.  Transfer of Electrophilic NH Using Convenient Sources of Ammonia: Direct Synthesis of NH Sulfoximines from Sulfoxides.

Authors:  Marina Zenzola; Robert Doran; Leonardo Degennaro; Renzo Luisi; James A Bull
Journal:  Angew Chem Int Ed Engl       Date:  2016-04-29       Impact factor: 15.336

10.  Catalytic Chemoselective Sulfimidation with an Electrophilic [CoIII (TAML)]- -Nitrene Radical Complex*.

Authors:  Nicolaas P van Leest; Jarl Ivar van der Vlugt; Bas de Bruin
Journal:  Chemistry       Date:  2020-11-19       Impact factor: 5.236

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