Literature DB >> 12822984

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

Robert E Maleczka1, Feng Shi, Daniel Holmes, Milton R Smith.   

Abstract

An efficient one-pot C-H activation/borylation/oxidation protocol for the preparation of phenols is described. This method is particularly attractive for the generation of meta-substituted phenols bearing ortho-/para-directing groups, as such substrates are difficult to access by other phenol syntheses.

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Year:  2003        PMID： 12822984     DOI： 10.1021/ja0349857

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  33 in total

1.  PyDipSi: a general and easily modifiable/traceless Si-tethered directing group for C-H acyloxylation of arenes.

Authors:  Natalia Chernyak; Alexander S Dudnik; Chunhui Huang; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2010-06-23       Impact factor: 15.419

2.  Heterocyclic chemistry: New reactivity realized.

Authors:  Timothy C Gallagher
Journal:  Nat Chem       Date:  2009-08       Impact factor: 24.427

3.  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

4.  Iridium-Catalyzed Silylation of C-H Bonds in Unactivated Arenes: A Sterically Encumbered Phenanthroline Ligand Accelerates Catalysis.

Authors:  Caleb Karmel; Zhewei Chen; John F Hartwig
Journal:  J Am Chem Soc       Date:  2019-04-23       Impact factor: 15.419

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

Authors:  A Monica Norberg; Milton R Smith; Robert E Maleczka
Journal:  Synthesis (Stuttg)       Date:  2011-02-18       Impact factor: 3.157

6.  Iridium-Catalyzed Silylation of Five-Membered Heteroarenes: High Sterically Derived Selectivity from a Pyridyl-Imidazoline Ligand.

Authors:  Caleb Karmel; Camille Z Rubel; Elena V Kharitonova; John F Hartwig
Journal:  Angew Chem Weinheim Bergstr Ger       Date:  2020-01-22

7.  Meta-selective C-H functionalization using a nitrile-based directing group and cleavable Si-tether.

Authors:  Sunggi Lee; Hyelee Lee; Kian L Tan
Journal:  J Am Chem Soc       Date:  2013-12-10       Impact factor: 15.419

8.  Aerobic oxidative Heck/dehydrogenation reactions of cyclohexenones: efficient access to meta-substituted phenols.

Authors:  Yusuke Izawa; Changwu Zheng; Shannon S Stahl
Journal:  Angew Chem Int Ed Engl       Date:  2013-02-19       Impact factor: 15.336

9.  The Pyridyldiisopropylsilyl Group: A Masked Functionality and Directing Group for Monoselective ortho-Acyloxylation and ortho-Halogenation Reactions of Arenes.

Authors:  Chunhui Huang; Natalia Chernyak; Alexander S Dudnik; Vladimir Gevorgyan
Journal:  Adv Synth Catal       Date:  2011-05-01       Impact factor: 5.837

10.  Harnessing C-H Borylation/Deborylation for Selective Deuteration, Synthesis of Boronate Esters, and Late Stage Functionalization.

Authors:  Venkata A Kallepalli; Kristin A Gore; Feng Shi; Luis Sanchez; Ghayoor A Chotana; Susanne L Miller; Robert E Maleczka; Milton R Smith
Journal:  J Org Chem       Date:  2015-08-07       Impact factor: 4.354
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