Literature DB >> 11796071

Regioselective oxidation of phenols to o-quinones with o-iodoxybenzoic acid (IBX).

Derek Magdziak1, Andy A Rodriguez, Ryan W Van De Water, Thomas R R Pettus.   

Abstract

[reaction: see text] An efficient regioselective method for oxidation of phenols to o-quinones is reported. When this procedure is combined with a subsequent reduction, it proves to be useful for the construction of a variety of catechols.

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Year:  2002        PMID： 11796071      PMCID： PMC1557836          DOI： 10.1021/ol017068j

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


  3 in total

1.  Selective oxidation at carbon adjacent to aromatic systems with IBX.

Authors:  K C Nicolaou; P S Baran; Y L Zhong
Journal:  J Am Chem Soc       Date:  2001-04-04       Impact factor: 15.419

2.  A mild anionic method for generating o-quinone methides: facile preparations of ortho-functionalized phenols.

Authors:  R M Jones; R W Van De Water; C C Lindsey; C Hoarau; T Ung; T R Pettus
Journal:  J Org Chem       Date:  2001-05-18       Impact factor: 4.354

3.  Synthesis of (+/-)-epoxysorbicillinol using a novel cyclohexa-2,5-dienone with synthetic applications to other sorbicillin derivatives.

Authors:  L H Pettus; R W Van De Water; T R Pettus
Journal:  Org Lett       Date:  2001-03-22       Impact factor: 6.005
  3 in total
  26 in total

1.  The naphthol selective estrogen receptor modulator (SERM), LY2066948, is oxidized to an o-quinone analogous to the naphthol equine estrogen, equilenin.

Authors:  Teshome B Gherezghiher; Bradley Michalsen; R Esala P Chandrasena; Zhihui Qin; Johann Sohn; Gregory R J Thatcher; Judy L Bolton
Journal:  Chem Biol Interact       Date:  2012-01-28       Impact factor: 5.192

2.  Catalytic, asymmetric reactions of ketenes and ketene enolates.

Authors:  Daniel H Paull; Anthony Weatherwax; Thomas Lectka
Journal:  Tetrahedron       Date:  2009-08-22       Impact factor: 2.457

Review 3.  Chemistry of polyvalent iodine.

Authors:  Viktor V Zhdankin; Peter J Stang
Journal:  Chem Rev       Date:  2008-12       Impact factor: 60.622

4.  Regiospecific oxidation of polycyclic aromatic phenols to quinones by hypervalent iodine reagents.

Authors:  Anhui Wu; Yazhen Duan; Daiwang Xu; Trevor M Penning; Ronald G Harvey
Journal:  Tetrahedron       Date:  2010-03-20       Impact factor: 2.457

5.  L-DOPA-quinone Mediated Recovery from GIRK Channel Firing Inhibition in Dopaminergic Neurons.

Authors:  Bruno M Bizzarri; Lorenzo Botta; Daniela Aversa; Nicola B Mercuri; Giulio Poli; Alessandro Barbieri; Nicola Berretta; Raffaele Saladino
Journal:  ACS Med Chem Lett       Date:  2019-01-09       Impact factor: 4.345

6.  Selective oxidation of 8,8'-hydroxylated binaphthols to bis-spironaphthalenones or binaphtho-para- and binaphtho-ortho-quinones.

Authors:  Erin E Podlesny; Patrick J Carroll; Marisa C Kozlowski
Journal:  Org Lett       Date:  2012-08-31       Impact factor: 6.005

7.  Asymmetric oxidative dearomatizations promoted by hypervalent iodine(III) reagents: an opportunity for rational catalyst design?

Authors:  Andrew M Harned
Journal:  Tetrahedron Lett       Date:  2014-08-20       Impact factor: 2.415

8.  Asymmetric oxidation of o-alkylphenols with chiral 2-(o-iodoxyphenyl)-oxazolines.

Authors:  Jagadish K Boppisetti; Vladimir B Birman
Journal:  Org Lett       Date:  2009-03-19       Impact factor: 6.005

9.  (±)-Diinsininone: made nature's way.

Authors:  Carolyn Selenski; Thomas R R Pettus
Journal:  Tetrahedron       Date:  2006-05-29       Impact factor: 2.457

10.  Synthesis of phenol and quinone metabolites of benzo[a]pyrene, a carcinogenic component of tobacco smoke implicated in lung cancer.

Authors:  Daiwang Xu; Trevor M Penning; Ian A Blair; Ronald G Harvey
Journal:  J Org Chem       Date:  2009-01-16       Impact factor: 4.354
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