Literature DB >> 26918863

Brønsted Acid-Mediated Hydrative Arylation of Unactivated Alkynes.

Daniel Kaiser1, Luís F Veiros2, Nuno Maulide3.   

Abstract

The Brønsted acid-mediated reaction of unactivated alkynes with aryl sulfoxides leads to simultaneous hydration and intermolecular C-C bond formation. This solvent- and metal-free transformation directly delivers α-arylated carbonyl compounds as the products of a formal hydrative arylation in an atom-economical manner. The products bear useful synthetic handles for further functionalization.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkynes; arylation; organic chemistry; rearrangement; sulfoxides

Year:  2016        PMID： 26918863     DOI： 10.1002/chem.201600432

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


  7 in total

1.  Catalytic Alkyne Arylation Using Traceless Directing Groups.

Authors:  Jung-Woo Park; Bubwoong Kang; Vy M Dong
Journal:  Angew Chem Int Ed Engl       Date:  2018-09-11       Impact factor: 15.336

2.  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

3.  α-Functionalisation of Ketones Through Metal-Free Electrophilic Activation.

Authors:  Wojciech Zawodny; Christopher J Teskey; Magdalena Mishevska; Martin Völkl; Boris Maryasin; Leticia González; Nuno Maulide
Journal:  Angew Chem Int Ed Engl       Date:  2020-09-11       Impact factor: 15.336

4.  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

5.  Synthesis of α-heterosubstituted ketones through sulfur mediated difunctionalization of internal alkynes.

Authors:  Zhong Zhang; Yuzheng Luo; Hongguang Du; Jiaxi Xu; Pingfan Li
Journal:  Chem Sci       Date:  2019-04-16       Impact factor: 9.825

6.  Vinyl Cation Stabilization by Silicon Enables a Formal Metal-Free α-Arylation of Alkyl Ketones.

Authors:  Amandine Pons; Jean Michalland; Wojciech Zawodny; Yong Chen; Veronica Tona; Nuno Maulide
Journal:  Angew Chem Int Ed Engl       Date:  2019-10-22       Impact factor: 15.336

7.  Chemoselective Alpha-Deuteration of Amides via Retro-ene Reaction.

Authors:  Vincent Porte; Giovanni Di Mauro; Manuel Schupp; Daniel Kaiser; Nuno Maulide
Journal:  Chemistry       Date:  2020-11-17       Impact factor: 5.020
  7 in total

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