Literature DB >> 10930251

Amidation of saturated C-H bonds catalyzed by electron-deficient ruthenium and manganese porphyrins. A highly catalytic nitrogen atom transfer process.

X Q Yu1, J S Huang, X G Zhou, C M Che.   

Abstract

Amidation of a variety of hydrocarbons with PhI=NTs catalyzed by ruthenium and manganese meso-tetrakis(pentafluorophenyl)porphyrins 1 and 2 afforded N-substituted amides in up to 92% yields with good to excellent substrate conversions. By employing catalyst 2, exceptionally high turnovers (up to 2600) were achieved, and the amidations can be effected by directly using PhI(OAc)(2)/NH(2)R as amidating reagents; in the case of R = COCF(3) a direct amination was realized in up to 90% yield.

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Year:  2000        PMID: 10930251     DOI: 10.1021/ol000107r

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


  21 in total

1.  Intermolecular Ritter-type C-H amination of unactivated sp3 carbons.

Authors:  Quentin Michaudel; Damien Thevenet; Phil S Baran
Journal:  J Am Chem Soc       Date:  2012-01-27       Impact factor: 15.419

2.  Catalytic intermolecular linear allylic C-H amination via heterobimetallic catalysis.

Authors:  Sean A Reed; M Christina White
Journal:  J Am Chem Soc       Date:  2008-02-27       Impact factor: 15.419

3.  Mechanism and Dynamics of Intramolecular C-H Insertion Reactions of 1-Aza-2-azoniaallene Salts.

Authors:  Xin Hong; Daniel A Bercovici; Zhongyue Yang; Nezar Al-Bataineh; Ramya Srinivasan; Ram C Dhakal; K N Houk; Matthias Brewer
Journal:  J Am Chem Soc       Date:  2015-07-07       Impact factor: 15.419

4.  Capturing fleeting intermediates in a catalytic C-H amination reaction cycle.

Authors:  Richard H Perry; Thomas J Cahill; Jennifer L Roizen; Justin Du Bois; Richard N Zare
Journal:  Proc Natl Acad Sci U S A       Date:  2012-10-22       Impact factor: 11.205

5.  Three-coordinate terminal imidoiron(III) complexes: structure, spectroscopy, and mechanism of formation.

Authors:  Ryan E Cowley; Nathan J DeYonker; Nathan A Eckert; Thomas R Cundari; Serena DeBeer; Eckhard Bill; Xavier Ottenwaelder; Christine Flaschenriem; Patrick L Holland
Journal:  Inorg Chem       Date:  2010-07-05       Impact factor: 5.165

6.  Ir-Catalyzed Intermolecular Branch-Selective Allylic C-H Amidation of Unactivated Terminal Olefins.

Authors:  Honghui Lei; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2019-02-04       Impact factor: 15.419

Review 7.  Complementary Strategies for Directed C(sp3 )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

Authors:  John C K Chu; Tomislav Rovis
Journal:  Angew Chem Int Ed Engl       Date:  2017-12-05       Impact factor: 15.336

8.  Rhodium-Catalyzed C-H Amination - An Enabling Method for Chemical Synthesis.

Authors:  J Du Bois
Journal:  Org Process Res Dev       Date:  2011-07-15       Impact factor: 3.317

Review 9.  Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion.

Authors:  Huw M L Davies; James R Manning
Journal:  Nature       Date:  2008-01-24       Impact factor: 49.962

10.  Intramolecular C(sp(3))H amination of arylsulfonyl azides with engineered and artificial myoglobin-based catalysts.

Authors:  Melanie Bordeaux; Ritesh Singh; Rudi Fasan
Journal:  Bioorg Med Chem       Date:  2014-05-20       Impact factor: 3.641

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