Literature DB >> 26536374

Remote Oxidation of Aliphatic C-H Bonds in Nitrogen-Containing Molecules.

Jennifer M Howell1, Kaibo Feng1, Joseph R Clark1, Louis J Trzepkowski1, M Christina White1.   

Abstract

Nitrogen heterocycles are ubiquitous in natural products and pharmaceuticals. Herein, we disclose a nitrogen complexation strategy that employs a strong Brønsted acid (HBF4) or an azaphilic Lewis acid (BF3) to enable remote, non-directed C(sp(3))-H oxidations of tertiary, secondary, and primary amine- and pyridine-containing molecules with tunable iron catalysts. Imides resist oxidation and promote remote functionalization.

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Year:  2015        PMID： 26536374      PMCID： PMC4924472          DOI： 10.1021/jacs.5b10299

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


  24 in total

1.  The oxidative mannich reaction catalyzed by dirhodium caprolactamate.

Authors:  Arthur J Catino; Jason M Nichols; Brian J Nettles; Michael P Doyle
Journal:  J Am Chem Soc       Date:  2006-05-03       Impact factor: 15.419

2.  Chemistry. Adding aliphatic C-H bond oxidations to synthesis.

Authors:  M Christina White
Journal:  Science       Date:  2012-02-17       Impact factor: 47.728

3.  Amine- and phosphine-borane adducts: new interest in old molecules.

Authors:  Anne Staubitz; Alasdair P M Robertson; Matthew E Sloan; Ian Manners
Journal:  Chem Rev       Date:  2010-07-14       Impact factor: 60.622

4.  Psychosedative agents. 2. 8-(4-Substituted 1-piperazinylalkyl)-8-azaspiro(4.5)decane-7,9-diones.

Authors:  L E Allen; H C Ferguson; J W Kissel
Journal:  J Med Chem       Date:  1972-05       Impact factor: 7.446

5.  Eosin Y catalyzed visible light oxidative C-C and C-P bond formation.

Authors:  Durga Prasad Hari; Burkhard König
Journal:  Org Lett       Date:  2011-07-11       Impact factor: 6.005

6.  New structural concepts for narcotic antagonists defined in a 4-phenylpiperidine series.

Authors:  D M Zimmerman; R Nickander; J S Horng; D T Wong
Journal:  Nature       Date:  1978-09-28       Impact factor: 49.962

7.  Ammonium-directed olefinic epoxidation: kinetic and mechanistic insights.

Authors:  Méabh B Brennan; Timothy D W Claridge; Richard G Compton; Stephen G Davies; Ai M Fletcher; Martin C Henstridge; David S Hewings; Wataru Kurosawa; James A Lee; Paul M Roberts; Anne K Schoonen; James E Thomson
Journal:  J Org Chem       Date:  2012-08-13       Impact factor: 4.354

8.  Site-selective aliphatic C-H bromination using N-bromoamides and visible light.

Authors:  Valerie A Schmidt; Ryan K Quinn; Andrew T Brusoe; Erik J Alexanian
Journal:  J Am Chem Soc       Date:  2014-10-03       Impact factor: 15.419

9.  Tuning reactivity and mechanism in oxidation reactions by mononuclear nonheme iron(IV)-oxo complexes.

Authors:  Wonwoo Nam; Yong-Min Lee; Shunichi Fukuzumi
Journal:  Acc Chem Res       Date:  2014-02-13       Impact factor: 22.384

Review 10.  Ethosuximide: from bench to bedside.

Authors:  M Zafer Gören; Filiz Onat
Journal:  CNS Drug Rev       Date:  2007
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  41 in total

1.  Second-Generation Palladium Catalyst System for Transannular C-H Functionalization of Azabicycloalkanes.

Authors:  Pablo J Cabrera; Melissa Lee; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2018-04-13       Impact factor: 15.419

2.  Combined Photoredox/Enzymatic C-H Benzylic Hydroxylations.

Authors:  Rick C Betori; Catherine M May; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-26       Impact factor: 15.336

3.  Remote C(sp3)-H Oxygenation of Protonated Aliphatic Amines with Potassium Persulfate.

Authors:  Melissa Lee; Melanie S Sanford
Journal:  Org Lett       Date:  2017-01-17       Impact factor: 6.005

4.  A General Strategy for Aliphatic C-H Functionalization Enabled by Organic Photoredox Catalysis.

Authors:  Kaila A Margrey; William L Czaplyski; David A Nicewicz; Erik J Alexanian
Journal:  J Am Chem Soc       Date:  2018-03-16       Impact factor: 15.419

5.  Selective Hydrogen Atom Abstraction through Induced Bond Polarization: Direct α-Arylation of Alcohols through Photoredox, HAT, and Nickel Catalysis.

Authors:  Jack Twilton; Melodie Christensen; Daniel A DiRocco; Rebecca T Ruck; Ian W Davies; David W C MacMillan
Journal:  Angew Chem Int Ed Engl       Date:  2018-04-06       Impact factor: 15.336

6.  Homobenzylic Oxygenation Enabled by Dual Organic Photoredox and Cobalt Catalysis.

Authors:  Joshua B McManus; Jeremy D Griffin; Alexander R White; David A Nicewicz
Journal:  J Am Chem Soc       Date:  2020-06-02       Impact factor: 15.419

7.  Remote, Late-Stage Oxidation of Aliphatic C-H Bonds in Amide-Containing Molecules.

Authors:  Takeshi Nanjo; Emilio C de Lucca; M Christina White
Journal:  J Am Chem Soc       Date:  2017-10-04       Impact factor: 15.419

Review 8.  Applications of Nonenzymatic Catalysts to the Alteration of Natural Products.

Authors:  Christopher R Shugrue; Scott J Miller
Journal:  Chem Rev       Date:  2017-06-05       Impact factor: 60.622

9.  Iron-Catalyzed Oxyfunctionalization of Aliphatic Amines at Remote Benzylic C-H Sites.

Authors:  Curren T Mbofana; Eugene Chong; James Lawniczak; Melanie S Sanford
Journal:  Org Lett       Date:  2016-08-16       Impact factor: 6.005

10.  Late-stage oxidative C(sp3)-H methylation.

Authors:  Kaibo Feng; Raundi E Quevedo; Jeffrey T Kohrt; Martins S Oderinde; Usa Reilly; M Christina White
Journal:  Nature       Date:  2020-03-16       Impact factor: 49.962
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