Literature DB >> 21413105

If C-H bonds could talk: selective C-H bond oxidation.

Timothy Newhouse1, Phil S Baran.   

Abstract

C-H oxidation has a long history and an ongoing presence in research at the forefront of chemistry and interrelated fields. As such, numerous highly useful articles and reviews have been written on this subject. Logically, these are generally written from the perspective of the scope and limitations of the reagents employed. This Minireview instead attempts to emphasize chemoselectivity imposed by the nature of the substrate. Consequently, many landmark discoveries in the field of C-H oxidation are not discussed, but hopefully the perspective taken herein will allow C-H oxidation reactions to be more readily incorporated into synthetic planning.
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2011        PMID: 21413105      PMCID: PMC3980681          DOI: 10.1002/anie.201006368

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  152 in total

1.  Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon-hydrogen bonds.

Authors:  Dmitry Shabashov; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2010-03-24       Impact factor: 15.419

Review 2.  Sigma-chelation-directed C-H functionalizations using Pd(II) and Cu(II) catalysts: regioselectivity, stereoselectivity and catalytic turnover.

Authors:  Jin-Quan Yu; Ramesh Giri; Xiao Chen
Journal:  Org Biomol Chem       Date:  2006-11-21       Impact factor: 3.876

3.  Mechanisms of C-H bond activation: rich synergy between computation and experiment.

Authors:  Youcef Boutadla; David L Davies; Stuart A Macgregor; Amalia I Poblador-Bahamonde
Journal:  Dalton Trans       Date:  2009-06-10       Impact factor: 4.390

4.  Mechanism of benzoquinone-promoted palladium-catalyzed oxidative cross-coupling reactions.

Authors:  Kami L Hull; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2009-07-22       Impact factor: 15.419

5.  Total synthesis of (+)-chaetocin and its analogues: their histone methyltransferase G9a inhibitory activity.

Authors:  Eriko Iwasa; Yoshitaka Hamashima; Shinya Fujishiro; Eisuke Higuchi; Akihiro Ito; Minoru Yoshida; Mikiko Sodeoka
Journal:  J Am Chem Soc       Date:  2010-03-31       Impact factor: 15.419

6.  C-H bond functionalization in complex organic synthesis.

Authors:  Kamil Godula; Dalibor Sames
Journal:  Science       Date:  2006-04-07       Impact factor: 47.728

7.  Oxidative C-H activation/C-C bond forming reactions: synthetic scope and mechanistic insights.

Authors:  Dipannita Kalyani; Nicholas R Deprez; Lopa V Desai; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2005-05-25       Impact factor: 15.419

8.  Ligand-modulated palladium-catalyzed aerobic alcohol oxidations.

Authors:  Matthew S Sigman; David R Jensen
Journal:  Acc Chem Res       Date:  2006-03       Impact factor: 22.384

9.  Bimetallic palladium catalysis: direct observation of Pd(III)-Pd(III) intermediates.

Authors:  David C Powers; Matthias A L Geibel; Johannes E M N Klein; Tobias Ritter
Journal:  J Am Chem Soc       Date:  2009-12-02       Impact factor: 15.419

10.  A mild, catalytic, and highly selective method for the oxidation of alpha,beta-enones to 1,4-enediones.

Authors:  Jin-Quan Yu; E J Corey
Journal:  J Am Chem Soc       Date:  2003-03-19       Impact factor: 15.419

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  144 in total

1.  Silicon-Tethered Strategies for C-H Functionalization Reactions.

Authors:  Marvin Parasram; Vladimir Gevorgyan
Journal:  Acc Chem Res       Date:  2017-08-03       Impact factor: 22.384

2.  Lessons and revelations from biomimetic syntheses.

Authors:  Mina Razzak; Jef K De Brabander
Journal:  Nat Chem Biol       Date:  2011-11-15       Impact factor: 15.040

3.  Overcoming the "oxidant problem": strategies to use O2 as the oxidant in organometallic C-H oxidation reactions catalyzed by Pd (and Cu).

Authors:  Alison N Campbell; Shannon S Stahl
Journal:  Acc Chem Res       Date:  2012-01-23       Impact factor: 22.384

4.  Catalysis: Disguise gets a reaction.

Authors:  Danielle M Schultz; John P Wolfe
Journal:  Nature       Date:  2012-02-29       Impact factor: 49.962

5.  O-H hydrogen bonding promotes H-atom transfer from α C-H bonds for C-alkylation of alcohols.

Authors:  Jenna L Jeffrey; Jack A Terrett; David W C MacMillan
Journal:  Science       Date:  2015-08-27       Impact factor: 47.728

6.  Controllable, Sequential, and Stereoselective C-H Allylic Alkylation of Alkenes.

Authors:  Ling Qin; Mohammed Sharique; Uttam K Tambar
Journal:  J Am Chem Soc       Date:  2019-10-15       Impact factor: 15.419

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.  Oxidative Entry into the Illicium Sesquiterpenes: Enantiospecific Synthesis of (+)-Pseudoanisatin.

Authors:  Kevin Hung; Matthew L Condakes; Takahiro Morikawa; Thomas J Maimone
Journal:  J Am Chem Soc       Date:  2016-12-16       Impact factor: 15.419

9.  Direct C-C Bond Formation from Alkanes Using Ni-Photoredox Catalysis.

Authors:  Laura K G Ackerman; Jesus I Martinez Alvarado; Abigail G Doyle
Journal:  J Am Chem Soc       Date:  2018-10-16       Impact factor: 15.419

10.  Total synthesis of Δ¹²-prostaglandin J₃, a highly potent and selective antileukemic agent.

Authors:  K C Nicolaou; Philipp Heretsch; Abdelatif ElMarrouni; Christopher R H Hale; Kiran K Pulukuri; Avinash K Kudva; Vivek Narayan; K Sandeep Prabhu
Journal:  Angew Chem Int Ed Engl       Date:  2014-08-05       Impact factor: 15.336

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