Literature DB >> 16209476

Bismuth-catalyzed benzylic oxidations with tert-butyl hydroperoxide.

Yannick Bonvin1, Emmanuel Callens, Igor Larrosa, David A Henderson, James Oldham, Andrew J Burton, Anthony G M Barrett.   

Abstract

[reaction: see text] Oxidation of alkyl and cycloalkyl arenes with tert-butyl hydroperoxide catalyzed by bismuth and picolinic acid in pyridine and acetic acid gave the corresponding benzylic ketones (48-99%). Alternatively, oxidation of methyl arenes gave the corresponding substituted benzoic acids (50-95%). Preliminary mechanistic studies were consistent with a radical mechanism rather than a bismuth(III)-bismuth(V) cycle.

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Year:  2005        PMID: 16209476     DOI: 10.1021/ol051765k

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


  7 in total

1.  A Highly Selective Vanadium Catalyst for Benzylic C-H Oxidation.

Authors:  Ji-Bao Xia; Kevin W Cormier; Chuo Chen
Journal:  Chem Sci       Date:  2012-04-13       Impact factor: 9.825

2.  Main Group Redox Catalysis of Organopnictogens: Vertical Periodic Trends and Emerging Opportunities in Group 15.

Authors:  Jeffrey M Lipshultz; Gen Li; Alexander T Radosevich
Journal:  J Am Chem Soc       Date:  2021-01-19       Impact factor: 15.419

3.  Base metal-catalyzed benzylic oxidation of (aryl)(heteroaryl)methanes with molecular oxygen.

Authors:  Hans Sterckx; Johan De Houwer; Carl Mensch; Wouter Herrebout; Kourosch Abbaspour Tehrani; Bert U W Maes
Journal:  Beilstein J Org Chem       Date:  2016-01-27       Impact factor: 2.883

4.  SnCl2/TiCl3-mediated deoximation of oximes in an aqueous solvent.

Authors:  Mei-Huey Lin; Han-Jun Liu; Cheng-Yu Chang; Wei-Cheng Lin; Tsung-Hsun Chuang
Journal:  Molecules       Date:  2012-03-01       Impact factor: 4.411

5.  Site-selective unidirectional benzylic sp3 C-H oxidation of dodecahydrotriphenylene with RuCl3-NaIO4: formation of benzylic ketones.

Authors:  Gaurang J Bhatt; Pradeep T Deota; Deepak Upadhyay; Prafulla K Jha
Journal:  RSC Adv       Date:  2021-10-20       Impact factor: 3.361

6.  Cobalt(ii)-catalyzed benzylic oxidations with potassium persulfate in TFA/TFAA.

Authors:  Tianlei Li; Jishun Li; Zihao Zhu; Weidong Pan; Song Wu
Journal:  RSC Adv       Date:  2019-07-04       Impact factor: 3.361

Review 7.  Benzylic Methylene Functionalizations of Diarylmethanes.

Authors:  Upma Gulati; Radhika Gandhi; Joydev K Laha
Journal:  Chem Asian J       Date:  2020-09-09
  7 in total

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