Literature DB >> 26610069

Gold-Catalyzed C-H Annulation of Anthranils with Alkynes: A Facile, Flexible, and Atom-Economical Synthesis of Unprotected 7-Acylindoles.

Hongming Jin1, Long Huang1, Jin Xie1, Matthias Rudolph1, Frank Rominger1, A Stephen K Hashmi2,3.   

Abstract

The gold-catalyzed C-H annulation of anthranil derivatives with alkynes offers a facile, flexible, and atom-economical one-step route to unprotected 7-acylindoles. An intermediate α-imino gold carbene, generated by an intermolecular reaction, promotes ortho-aryl C-H functionalization to afford the target products. The transformation proceeds with a broad range of substrates under mild conditions. Moreover, the obtained functionalized indole products represent a versatile platform for the construction of diverse indolyl frameworks.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CH functionalization; alkynes; gold carbenoids; gold catalysis; indoles

Year:  2015        PMID： 26610069     DOI： 10.1002/anie.201508309

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  15 in total

1.  Gold(I)-Catalyzed Synthesis of 3-Sulfenyl Pyrroles and Indoles by a Regioselective Annulation of Alkynyl Thioethers.

Authors:  Peter E Simm; Prakash Sekar; Jeffery Richardson; Paul W Davies
Journal:  ACS Catal       Date:  2021-05-13       Impact factor: 13.084

2.  Diverting Reactive Intermediates Toward Unusual Chemistry: Unexpected Anthranil Products from Davis-Beirut Reaction.

Authors:  Jie S Zhu; Jung-Ho Son; Andrew P Teuthorn; Makhluf J Haddadin; Mark J Kurth; Dean J Tantillo
Journal:  J Org Chem       Date:  2017-09-28       Impact factor: 4.354

3.  Synthesis and structures of gold and copper carbene intermediates in catalytic amination of alkynes.

Authors:  Jiwei Wang; Xiaoming Cao; Shichang Lv; Caiyun Zhang; Sheng Xu; Min Shi; Jun Zhang
Journal:  Nat Commun       Date:  2017-03-06       Impact factor: 14.919

4.  Alkynyl Thioethers in Gold-Catalyzed Annulations To Form Oxazoles.

Authors:  Raju Jannapu Reddy; Matthew P Ball-Jones; Paul W Davies
Journal:  Angew Chem Int Ed Engl       Date:  2017-09-19       Impact factor: 15.336

5.  A novel Pd-catalysed sequential carbonylation/cyclization approach toward bis-N-heterocycles: rationalization by electronic structure calculations.

Authors:  Liliana Damas; Rui M B Carrilho; Sandra C C Nunes; Alberto A C C Pais; László Kollár; Marta Pineiro; Mariette M Pereira
Journal:  R Soc Open Sci       Date:  2018-09-12       Impact factor: 2.963

6.  Au-catalyzed skeletal rearrangement of O-propargylic oximes via N-O bond cleavage with the aid of a Brønsted base cocatalyst.

Authors:  Keigo Shiga; Ilya D Gridnev; Masahiro Terada; Itaru Nakamura
Journal:  Chem Sci       Date:  2019-04-18       Impact factor: 9.825

7.  Gold-catalyzed (4+3)-annulations of 2-alkenyl-1-alkynylbenzenes with anthranils with alkyne-dependent chemoselectivity: skeletal rearrangement versus non-rearrangement.

Authors:  RahulKumar Rajmani Singh; Manisha Skaria; Liang-Yu Chen; Mu-Jeng Cheng; Rai-Shung Liu
Journal:  Chem Sci       Date:  2018-11-12       Impact factor: 9.825

8.  Gold-catalyzed bicyclic annulations of 4-methoxy-1,2-dienyl-5-ynes with isoxazoles to form indolizine derivatives via an Au-π-allene intermediate.

Authors:  Antony Sekar Kulandai Raj; Kuo-Chen Tan; Liang-Yu Chen; Mu-Jeng Cheng; Rai-Shung Liu
Journal:  Chem Sci       Date:  2019-05-22       Impact factor: 9.825

9.  Synthesis of benzothiophene and indole derivatives through metal-free propargyl-allene rearrangement and allyl migration.

Authors:  Jinzhong Yao; Yajie Xie; Lianpeng Zhang; Yujin Li; Hongwei Zhou
Journal:  Beilstein J Org Chem       Date:  2017-09-06       Impact factor: 2.883

10.  Gold-catalyzed (4 + 2)-annulations between α-alkyl alkenylgold carbenes and benzisoxazoles with reactive alkyl groups.

Authors:  Bhanudas Dattatray Mokar; Prakash D Jadhav; Y B Pandit; Rai-Shung Liu
Journal:  Chem Sci       Date:  2018-04-23       Impact factor: 9.825
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