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Literature DB >> 28753015

Synthesis of 1,2-Bis(trifluoromethylthio)arenes via Aryne Intermediates.

Abstract

A general method for synthesis of 1,2-bis-trifluoromethylthioarenes has been developed. Arynes generated from silyl aryl triflates or halides react with bis(trifluoromethyl)disulfide to afford 1,2-bis-trifluoromethylthioarenes. Aryl, alkyl, ester, halide, and methoxy functionalities are compatible with reaction conditions. Use of bis(perfluoroaryl)disulfides gave moderate yields of aryne disulfenylation or cyclization to fluorinated dibenzothiophenes.

Entities: Chemical Gene

Mesh：

Substances：

Year: 2017 PMID： 28753015 PMCID： PMC5716473 DOI： 10.1021/acs.orglett.7b01901

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

22 in total

1. Copper-catalyzed oxidative trifluoromethylthiolation of aryl boronic acids with TMSCF3 and elemental sulfur.

Authors: Chao Chen; Yan Xie; Lingling Chu; Ruo-Wen Wang; Xingang Zhang; Feng-Ling Qing
Journal: Angew Chem Int Ed Engl Date: 2012-01-27 Impact factor: 15.336

Review 2. Alpha-fluorinated ethers, thioethers, and amines: anomerically biased species.

Authors: Frédéric Leroux; Peter Jeschke; Manfred Schlosser
Journal: Chem Rev Date: 2005-03 Impact factor: 60.622

3. Trifluoromethylation of α-haloketones.

Authors: Petr Novák; Anton Lishchynskyi; Vladimir V Grushin
Journal: J Am Chem Soc Date: 2012-09-21 Impact factor: 15.419

4. Divergent Reaction Pathways for Phenol Arylation by Arynes: Synthesis of Helicenes and 2-Arylphenols.

Authors: Thanh Truong; Olafs Daugulis
Journal: Chem Sci Date: 2013 Impact factor: 9.825

5. Pd-catalyzed synthesis of Ar-SCF3 compounds under mild conditions.

Authors: Georgiy Teverovskiy; David S Surry; Stephen L Buchwald
Journal: Angew Chem Int Ed Engl Date: 2011-06-20 Impact factor: 15.336

6. Aromatic and heterocyclic perfluoroalkyl sulfides. Methods of preparation.

Authors: Vladimir N Boiko
Journal: Beilstein J Org Chem Date: 2010-08-18 Impact factor: 2.883

Review 7. Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001-2011).

Authors: Jiang Wang; María Sánchez-Roselló; José Luis Aceña; Carlos del Pozo; Alexander E Sorochinsky; Santos Fustero; Vadim A Soloshonok; Hong Liu
Journal: Chem Rev Date: 2013-12-03 Impact factor: 60.622

Synthesis of 1,2-Bis(trifluoromethylthio)arenes via Aryne Intermediates.

1. Copper-catalyzed oxidative trifluoromethylthiolation of aryl boronic acids with TMSCF3 and elemental sulfur.

Review 2. Alpha-fluorinated ethers, thioethers, and amines: anomerically biased species.

3. Trifluoromethylation of α-haloketones.

4. Divergent Reaction Pathways for Phenol Arylation by Arynes: Synthesis of Helicenes and 2-Arylphenols.

5. Pd-catalyzed synthesis of Ar-SCF3 compounds under mild conditions.

6. Aromatic and heterocyclic perfluoroalkyl sulfides. Methods of preparation.

Review 7. Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001-2011).

8. Active trifluoromethylating agents from well-defined Copper(I)-CF3 complexes.

9. Copper-promoted sulfenylation of sp2 C-H bonds.

10. Copper-catalyzed, directing group-assisted fluorination of arene and heteroarene C-H bonds.

1. 1,2-Bis(arylthio)arene synthesis via aryne intermediates.

2. Cascade trifluoromethylthiolation and cyclization of N-[(3-aryl)propioloyl]indoles.