Literature DB >> 22273364

Versatile synthesis of isocoumarins and α-pyrones by ruthenium-catalyzed oxidative C-H/O-H bond cleavages.

Lutz Ackermann1, Jola Pospech, Karolina Graczyk, Karsten Rauch.   

Abstract

An inexpensive cationic ruthenium(II) catalyst enabled the expedient synthesis of isocoumarins through oxidative annulations of alkynes by benzoic acids. This C-H/O-H bond functionalization process also proved applicable to the preparation of α-pyrones and was shown to proceed by rate-limiting C-H bond ruthenation.
© 2012 American Chemical Society

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Year:  2012        PMID: 22273364     DOI: 10.1021/ol2034614

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


  10 in total

1.  A decarboxylative approach for regioselective hydroarylation of alkynes.

Authors:  Jing Zhang; Ruja Shrestha; John F Hartwig; Pinjing Zhao
Journal:  Nat Chem       Date:  2016-09-05       Impact factor: 24.427

2.  Expeditious Synthesis of Isoquinolones and Isocoumarins with a Vinyl Borane as an Acetylene Equivalent.

Authors:  Momar Toure; Saul Jaime-Figueroa; George M Burslem; Craig M Crews
Journal:  European J Org Chem       Date:  2016-07-26

3.  A Strategy for Site- and Chemoselective C-H Alkenylation through Osmaelectrooxidative Catalysis.

Authors:  Isaac Choi; Antonis M Messinis; Xiaoyan Hou; Lutz Ackermann
Journal:  Angew Chem Int Ed Engl       Date:  2021-11-18       Impact factor: 16.823

4.  Synthesis of isocoumarins with different substituted patterns via Passerini-aldol sequence.

Authors:  Guan-Hua Ma; Bo Jiang; Xing-Jun Tu; Yi Ning; Shu-Jiang Tu; Guigen Li
Journal:  Org Lett       Date:  2014-08-20       Impact factor: 6.005

Review 5.  Recent advances in the synthesis of 2-pyrones.

Authors:  Jong Seok Lee
Journal:  Mar Drugs       Date:  2015-03-23       Impact factor: 5.118

6.  Merging rhodium-catalysed C-H activation and hydroamination in a highly selective [4+2] imine/alkyne annulation.

Authors:  Rajith S Manan; Pinjing Zhao
Journal:  Nat Commun       Date:  2016-06-20       Impact factor: 14.919

7.  Ru(II)-Catalyzed Regiospecific C-H/O-H Oxidative Annulation to Access Isochromeno[8,1-ab]phenazines: Far-Red Fluorescence and Live Cancer Cell Imaging.

Authors:  Sivakalai Mayakrishnan; Yuvaraj Arun; Chandrasekar Balachandran; Suresh Awale; Narayanan Uma Maheswari; Paramasivan Thirumalai Perumal
Journal:  ACS Omega       Date:  2017-06-17

8.  Mild, Selective Ru-Catalyzed Deuteration Using D2 O as a Deuterium Source.

Authors:  Pascal Eisele; Franziska Ullwer; Sven Scholz; Bernd Plietker
Journal:  Chemistry       Date:  2019-11-03       Impact factor: 5.236

9.  Divergent rhodium-catalyzed electrochemical vinylic C-H annulation of acrylamides with alkynes.

Authors:  Yi-Kang Xing; Xin-Ran Chen; Qi-Liang Yang; Shuo-Qing Zhang; Hai-Ming Guo; Xin Hong; Tian-Sheng Mei
Journal:  Nat Commun       Date:  2021-02-10       Impact factor: 14.919

10.  Rhodium(III)-Catalyzed Intramolecular Annulations of Acrylic and Benzoic Acids to Alkynes.

Authors:  David F Fernández; Noelia Casanova; José Luis Mascareñas; Moisés Gulías
Journal:  ACS Omega       Date:  2019-04-04
  10 in total

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