Literature DB >> 20687603

Synthesis of 3-trifluoromethylbenzo[b]furans from phenols via direct ortho functionalization by extended Pummerer reaction.

Takayuki Kobatake1, Daishi Fujino, Suguru Yoshida, Hideki Yorimitsu, Koichiro Oshima.   

Abstract

A concise and diversity-oriented route to trifluoromethylbenzo[b]furans has been devised. A variety of phenols are directly converted to the corresponding 2-methylthio-3-trifluoromethylbenzo[b]furans by new triflic-anhydride-mediated extended Pummerer annulation reactions with trifluoromethylketene dithioacetal monoxide. The methylthio group of the products undergoes further transformations, which increase the diversity of available trifluoromethylbenzo[b]furans.

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Year:  2010        PMID: 20687603     DOI: 10.1021/ja1030134

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


  12 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.  Synthesis of Pyrroles via Consecutive 6π-Electrocyclization/Ring-Contraction of Sulfilimines.

Authors:  Franz-Lucas Haut; Niklas J Feichtinger; Immanuel Plangger; Lukas A Wein; Mira Müller; Tim-Niclas Streit; Klaus Wurst; Maren Podewitz; Thomas Magauer
Journal:  J Am Chem Soc       Date:  2021-06-09       Impact factor: 15.419

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.  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

6.  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

7.  Sulfoxide-directed metal-free cross-couplings in the expedient synthesis of benzothiophene-based components of materials.

Authors:  Andrew J Eberhart; Harry Shrives; Yuntong Zhang; Amandine Carrër; Adam V S Parry; Daniel J Tate; Michael L Turner; David J Procter
Journal:  Chem Sci       Date:  2015-11-09       Impact factor: 9.825

Review 8.  Last Decade of Unconventional Methodologies for the Synthesis of Substituted Benzofurans.

Authors:  Lucia Chiummiento; Rosarita D'Orsi; Maria Funicello; Paolo Lupattelli
Journal:  Molecules       Date:  2020-05-16       Impact factor: 4.411

9.  Ortho-selective C-H arylation of phenols with N-carboxyindoles under Brønsted acid- or Cu(i)-catalysis.

Authors:  Nguyen H Nguyen; Soo Min Oh; Cheol-Min Park; Seunghoon Shin
Journal:  Chem Sci       Date:  2021-12-27       Impact factor: 9.825

10.  Palladium-Catalyzed Synthesis of 2,3-Disubstituted Benzofurans: An Approach Towards the Synthesis of Deuterium Labeled Compounds.

Authors:  Soumitra Agasti; Soham Maity; Kalman J Szabo; Debabrata Maiti
Journal:  Adv Synth Catal       Date:  2015-07-14       Impact factor: 5.837

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