Literature DB >> 21818793

α-Sulfonyl succinimides: versatile sulfinate donors in Fe-catalyzed, salt-free, neutral allylic substitution.

Markus Jegelka1, Bernd Plietker.   

Abstract

Allyl sulfones are versatile intermediates in organic chemistry. The presence of two distinct functional groups sets the stage for a plethora of subsequent transformations. However, despite these advantages the preparation of regioisomerically enriched sulfones is not easy. The use of sulfinate salts as nucleophiles in substitutions is frequently accompanied by side reactions such as π-bond migration, β-elimination, and so on. Herein we present a preparatively simple way to synthesize a variety of different aryl or alkyl allyl sulfones starting from readily accessible allylic carbonates. By employing aryl or alkyl α-sulfonyl succinimides as sulfinate synthons, mild and regioselective ipso substitution of diverse allylic carbonates was realized.
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Year:  2011        PMID: 21818793     DOI: 10.1002/chem.201101047

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  4 in total

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Journal:  RSC Adv       Date:  2020-08-21       Impact factor: 4.036

4.  Non-decarbonylative photochemical versus thermal activation of Bu4N[Fe(CO)3(NO)] - the Fe-catalyzed Cloke-Wilson rearrangement of vinyl and arylcyclopropanes.

Authors:  Che-Hung Lin; Dominik Pursley; Johannes E M N Klein; Johannes Teske; Jennifer A Allen; Fabian Rami; Andreas Köhn; Bernd Plietker
Journal:  Chem Sci       Date:  2015-09-03       Impact factor: 9.825

  4 in total

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