Literature DB >> 18680381

Meta- and para-difunctionalization of arenes via a sulfoxide-magnesium exchange reaction.

Christian B Rauhut1, Laurin Melzig, Paul Knochel.   

Abstract

The aryl sulfoxide moiety (ArSO) allows an expedient two-step meta-, para-difunctionalization of readily available diaryl sulfoxides. In the first step, the sulfoxide plays the role of a directing metalation group. In the second step, triggered by i-PrMgCl x LiCl, it becomes a leaving group and undergoes a regioselective sulfoxide-magnesium exchange.

Entities:  

Year:  2008        PMID: 18680381     DOI: 10.1021/ol801431z

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


  2 in total

1.  Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.

Authors:  Daniel Kaiser; Immo Klose; Rik Oost; James Neuhaus; Nuno Maulide
Journal:  Chem Rev       Date:  2019-06-25       Impact factor: 60.622

2.  Stereoselective synthesis of tetrasubstituted alkenes via a sequential carbocupration and a new sulfur-lithium exchange.

Authors:  Andreas Unsinn; Cora Dunst; Paul Knochel
Journal:  Beilstein J Org Chem       Date:  2012-12-18       Impact factor: 2.883

  2 in total

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