Literature DB >> 21859084

Insertion of arynes into thioureas: a new amidine synthesis.

Kallolmay Biswas1, Michael F Greaney.   

Abstract

Arynes, generated from trimethylsilyl phenyltriflate precursors, have been found to react with thioureas via a formal π-insertion into the C═S bond. The reaction contrasts with that of ureas, which proceeds via benzyne σ-insertion into the C-N bond, and represents a new, operationally simple route to functionalized amidines.
© 2011 American Chemical Society

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Year:  2011        PMID： 21859084     DOI： 10.1021/ol202049v

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


  11 in total

1.  Reactions of Hexadehydro-Diels-Alder (HDDA)-Derived Benzynes with Thioamides: Synthesis of Dihydrobenzothiazino-Heterocyclics.

Authors:  Vignesh Palani; Junhua Chen; Thomas R Hoye
Journal:  Org Lett       Date:  2016-12-01       Impact factor: 6.005

2.  Insertion of arynes into N-halo bonds: a direct approach to o-haloaminoarenes.

Authors:  Charles E Hendrick; Stacey L McDonald; Qiu Wang
Journal:  Org Lett       Date:  2013-06-24       Impact factor: 6.005

3.  Formation of acridones by ethylene extrusion in the reaction of arynes with β-lactams and dihydroquinolinones.

Authors:  Yuesi Fang; Donald C Rogness; Richard C Larock; Feng Shi
Journal:  J Org Chem       Date:  2012-07-10       Impact factor: 4.354

4.  Total syntheses of chelidonine and norchelidonine via an enamide-benzyne-[2 + 2] cycloaddition cascade.

Authors:  Zhi-Xiong Ma; John B Feltenberger; Richard P Hsung
Journal:  Org Lett       Date:  2012-05-10       Impact factor: 6.005

5.  Direct palladium(II)-catalyzed synthesis of arylamidines from aryltrifluoroborates.

Authors:  Jonas Sävmarker; Jonas Rydfjord; Johan Gising; Luke R Odell; Mats Larhed
Journal:  Org Lett       Date:  2012-04-17       Impact factor: 6.005

6.  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

7.  Three-component coupling reactions of arynes for the synthesis of benzofurans and coumarins.

Authors:  Eito Yoshioka; Shigeru Kohtani; Hideto Miyabe
Journal:  Molecules       Date:  2014-01-13       Impact factor: 4.411

Review 8.  Transition-Metal-Free Activation of Amide Bond by Arynes.

Authors:  Hideto Miyabe
Journal:  Molecules       Date:  2018-08-27       Impact factor: 4.411

9.  Decarboxylative palladium(II)-catalyzed synthesis of aryl amidines from aryl carboxylic acids: development and mechanistic investigation.

Authors:  Jonas Rydfjord; Fredrik Svensson; Alejandro Trejos; Per J R Sjöberg; Christian Sköld; Jonas Sävmarker; Luke R Odell; Mats Larhed
Journal:  Chemistry       Date:  2013-08-28       Impact factor: 5.236

10.  Metal Free Bi(hetero)aryl Synthesis: A Benzyne Truce-Smiles Rearrangement.

Authors:  Catherine M Holden; Shariar M A Sohel; Michael F Greaney
Journal:  Angew Chem Int Ed Engl       Date:  2016-01-13       Impact factor: 15.336
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