Literature DB >> 31328188

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

Milad Mesgar1, Justin Nguyen-Le, Olafs Daugulis.   

Abstract

Lithium 1,1-diadamantylamide (LDAM) base-promoted insertion of arynes into disulfide S-S bonds is described. After generation of arynes from readily available aryl halides and triflates, reactions with diaryl and diisopropyl disulfides afford the insertion products in moderate to excellent yields. Use of 1-cyclohexenyl triflate gave an excellent yield of 1,2-bis(phenylthio)cyclohexene.

Entities:  

Year:  2019        PMID： 31328188      PMCID： PMC6896799          DOI： 10.1039/c9cc03863a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  13 in total

1.  Synthesis of di-, tri-, and tetrasulfides through multifold carbon-sulfur cross-coupling reactions with indium tri(organothiolates) in a one-pot procedure.

Authors:  Phil Ho Lee; Youngchul Park; Sangkyun Park; Euijae Lee; Sunggak Kim
Journal:  J Org Chem       Date:  2011-01-12       Impact factor: 4.354

2.  Regioselective C-H Sulfanylation of Aryl Sulfoxides by Means of Pummerer-Type Activation.

Authors:  Hitomi Kawashima; Tomoyuki Yanagi; Chien-Chi Wu; Keisuke Nogi; Hideki Yorimitsu
Journal:  Org Lett       Date:  2017-08-15       Impact factor: 6.005

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

Authors:  Milad Mesgar; Olafs Daugulis
Journal:  Org Lett       Date:  2017-07-28       Impact factor: 6.005

4.  Concise Approach to Cyclohexyne and 1,2-Cyclohexadiene Precursors.

Authors:  Jason V Chari; Francesca M Ippoliti; Neil K Garg
Journal:  J Org Chem       Date:  2019-03-06       Impact factor: 4.354

5.  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

6.  New Hindered Amide Base for Aryne Insertion into Si-P, Si-S, Si-N, and C-C Bonds.

Authors:  Milad Mesgar; Justin Nguyen-Le; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2018-10-10       Impact factor: 15.419

7.  Rhodium-catalyzed substitution reaction of aryl fluorides with disulfides: p-orientation in the polyarylthiolation of polyfluorobenzenes.

Authors:  Mieko Arisawa; Takaaki Suzuki; Tomofumi Ishikawa; Masahiko Yamaguchi
Journal:  J Am Chem Soc       Date:  2008-08-23       Impact factor: 15.419

8.  Synthesis of p-Phenylene Sulfide Molecular Asterisks.

Authors:  Marc Gingras; Alain Pinchart; Carol Dallaire
Journal:  Angew Chem Int Ed Engl       Date:  1998-12-04       Impact factor: 15.336

9.  Double heteroatom functionalization of arenes using benzyne three-component coupling.

Authors:  José-Antonio García-López; Meliha Çetin; Michael F Greaney
Journal:  Angew Chem Int Ed Engl       Date:  2015-01-07       Impact factor: 15.336

10.  General method for functionalized polyaryl synthesis via aryne intermediates.

Authors:  Thanh Truong; Milad Mesgar; Ky Khac Anh Le; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2014-06-03       Impact factor: 15.419
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  2 in total

1.  The synthesis of N,N'-disulfanediyl-bis(N'-((E)-benzylidene)acetohydrazide) from (E)-N'-benzylideneacetohydrazide and S8.

Authors:  Hong-Yan Liu; Yu Chen; Li-Qiang Hao; Guo-Dong Wang; Hong-Shuang Li; Cheng-Cai Xia
Journal:  RSC Adv       Date:  2020-11-11       Impact factor: 4.036

2.  Synthesis and Structural Properties of Adamantane-Substituted Amines and Amides Containing an Additional Adamantane, Azaadamantane or Diamantane Moiety.

Authors:  Maxime Bonsir; Alan R Kennedy; Yves Geerts
Journal:  ChemistryOpen       Date:  2022-03-04       Impact factor: 2.630
  2 in total

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