Literature DB >> 27746513

Practical One-Pot C-H Activation/Borylation/Oxidation: Preparation of 3-Bromo-5-methylphenol on a Multigram Scale.

A Monica Norberg1, Milton R Smith1, Robert E Maleczka1.   

Abstract

A practical one-pot C-H activation/borylation/oxidation sequence for the generation of 3,5-disubstituted phenols is presented. Specifically, 3-bromo-5-methylphenol is prepared from 3-bromotoluene, without isolation of intermediates, on a multigram scale, and in high yield. The process proceeds under mild conditions and can be completed within one day.

Entities:  

Keywords:  C–H activation; boronic ester; borylation; oxidation; phenol

Year:  2011        PMID： 27746513      PMCID： PMC5062740          DOI： 10.1055/s-0030-1258443

Source DB:  PubMed          Journal:  Synthesis (Stuttg)        ISSN： 0039-7881            Impact factor:   3.157


  5 in total

1.  C-H activation for the construction of C-B bonds.

Authors:  Ibraheem A I Mkhalid; Jonathan H Barnard; Todd B Marder; Jaclyn M Murphy; John F Hartwig
Journal:  Chem Rev       Date:  2010-02-10       Impact factor: 60.622

2.  Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds.

Authors:  Jian-Yang Cho; Man Kin Tse; Daniel Holmes; Robert E Maleczka; Milton R Smith
Journal:  Science       Date:  2001-11-22       Impact factor: 47.728

3.  Mechanism of the mild functionalization of arenes by diboron reagents catalyzed by iridium complexes. Intermediacy and chemistry of bipyridine-ligated iridium trisboryl complexes.

Authors:  Timothy M Boller; Jaclyn M Murphy; Marko Hapke; Tatsuo Ishiyama; Norio Miyaura; John F Hartwig
Journal:  J Am Chem Soc       Date:  2005-10-19       Impact factor: 15.419

4.  Electronic effects in iridium C-H borylations: insights from unencumbered substrates and variation of boryl ligand substituents.

Authors:  Britt A Vanchura; Sean M Preshlock; Philipp C Roosen; Venkata A Kallepalli; Richard J Staples; Robert E Maleczka; Daniel A Singleton; Milton R Smith
Journal:  Chem Commun (Camb)       Date:  2010-09-20       Impact factor: 6.222

5.  C-H activation/borylation/oxidation: a one-pot unified route to meta-substituted phenols bearing ortho-/para-directing groups.

Authors:  Robert E Maleczka; Feng Shi; Daniel Holmes; Milton R Smith
Journal:  J Am Chem Soc       Date:  2003-07-02       Impact factor: 15.419
  5 in total
  2 in total

1.  Nitrile in the Hole: Discovery of a Small Auxiliary Pocket in Neuronal Nitric Oxide Synthase Leading to the Development of Potent and Selective 2-Aminoquinoline Inhibitors.

Authors:  Maris A Cinelli; Huiying Li; Georges Chreifi; Thomas L Poulos; Richard B Silverman
Journal:  J Med Chem       Date:  2017-04-19       Impact factor: 7.446

Review 2.  Indenylmetal Catalysis in Organic Synthesis.

Authors:  Barry M Trost; Michael C Ryan
Journal:  Angew Chem Int Ed Engl       Date:  2017-01-27       Impact factor: 15.336
  2 in total

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