Literature DB >> 23641807

Sulfur(IV)-mediated transformations: from ylide transfer to metal-free arylation of carbonyl compounds.

Xueliang Huang1, Mahendra Patil, Christophe Farès, Walter Thiel, Nuno Maulide.   

Abstract

The development of a direct ylide transfer to carbonyl derivatives and of a sulfoxide-mediated arylation is presented from a unified perspective. Mechanistic studies (including density functional calculations) support a common reaction pathway and showcase how subtle changes in reactant properties can lead to disparate and seemingly unrelated reaction outcomes.

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Year:  2013        PMID: 23641807     DOI: 10.1021/ja4017683

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  19 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.  The ketene-surrogate coupling: catalytic conversion of aryl iodides into aryl ketenes through ynol ethers.

Authors:  Wenhan Zhang; Joseph M Ready
Journal:  Angew Chem Int Ed Engl       Date:  2014-06-27       Impact factor: 15.336

3.  Sulfoxide-Directed Metal-Free ortho-Propargylation of Aromatics and Heteroaromatics.

Authors:  Andrew J Eberhart; Harry J Shrives; Estela Álvarez; Amandine Carrër; Yuntong Zhang; David J Procter
Journal:  Chemistry       Date:  2015-03-06       Impact factor: 5.236

4.  Nucleophilic ortho-allylation of pyrroles and pyrazoles: an accelerated Pummerer/thio-Claisen rearrangement sequence.

Authors:  Andrew J Eberhart; Claudio Cicoira; David J Procter
Journal:  Org Lett       Date:  2013-07-15       Impact factor: 6.005

5.  4-Trifluoromethyl-p-quinols as dielectrophiles: three-component, double nucleophilic addition/aromatization reactions.

Authors:  Jinhuan Dong; Lou Shi; Ling Pan; Xianxiu Xu; Qun Liu
Journal:  Sci Rep       Date:  2016-06-01       Impact factor: 4.379

6.  Synthesis of γ-pyrones via decarboxylative condensation of β-ketoacids.

Authors:  Jérémy Merad; Thomas Maier; Catarina A B Rodrigues; Nuno Maulide
Journal:  Monatsh Chem       Date:  2016-10-27       Impact factor: 1.451

7.  A bioinspired and biocompatible ortho-sulfiliminyl phenol synthesis.

Authors:  Feng Xiong; Liang Lu; Tian-Yu Sun; Qian Wu; Dingyuan Yan; Ying Chen; Xinhao Zhang; Wei Wei; Yi Lu; Wei-Yin Sun; Jie Jack Li; Jing Zhao
Journal:  Nat Commun       Date:  2017-06-19       Impact factor: 14.919

8.  Regioselective synthesis of C3 alkylated and arylated benzothiophenes.

Authors:  Harry J Shrives; José A Fernández-Salas; Christin Hedtke; Alexander P Pulis; David J Procter
Journal:  Nat Commun       Date:  2017-03-20       Impact factor: 14.919

9.  Metal-free O-H/C-H difunctionalization of phenols by o-hydroxyarylsulfonium salts in water.

Authors:  Dengfeng Chen; Qingyuan Feng; Yunqin Yang; Xu-Min Cai; Fei Wang; Shenlin Huang
Journal:  Chem Sci       Date:  2016-11-04       Impact factor: 9.825

10.  Dual vicinal functionalisation of heterocycles via an interrupted Pummerer coupling/[3,3]-sigmatropic rearrangement cascade.

Authors:  Mindaugas Šiaučiulis; Selma Sapmaz; Alexander P Pulis; David J Procter
Journal:  Chem Sci       Date:  2017-11-17       Impact factor: 9.825

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