Literature DB >> 25861123

Palladium-Catalyzed Ligand-Directed Oxidative Functionalization of Cyclopropanes.

Asako Kubota1, Melanie S Sanford1.   

Abstract

This report describes the Pd-catalyzed functionalization of cyclopropanes containing oxazoline, oxime ether, and pyridine directing groups. Three different oxidants were examined in these studies: IOAc, PhI(OAc)2, and benzoquinone. The reactions yielded products derived from 2° sp3 C-H functionalization and/or C-C activation of the cyclopropane ring. The outcome and the product distributions were highly dependent on the structure of the substrate and the nature of the oxidant.

Entities:  

Keywords:  C-H functionalization; cleavage; cyclopropane; homogeneous catalysis; palladium

Year:  2011        PMID: 25861123      PMCID: PMC4386895          DOI: 10.1055/s-0030-1260087

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


  29 in total

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2.  Palladium-catalyzed asymmetric iodination of unactivated C-H bonds under mild conditions.

Authors:  Ramesh Giri; Xiao Chen; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2005-03-29       Impact factor: 15.336

Review 3.  Heterocycles from cyclopropanes: applications in natural product synthesis.

Authors:  Cheryl A Carson; Michael A Kerr
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4.  Functionalization of organic molecules by transition-metal-catalyzed C(sp3)-H activation.

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Journal:  Chemistry       Date:  2010-03-01       Impact factor: 5.236

5.  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

6.  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

7.  Insights into directing group ability in palladium-catalyzed C-H bond functionalization.

Authors:  Lopa V Desai; Kara J Stowers; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2008-09-10       Impact factor: 15.419

8.  Pd(II)-catalyzed cross-coupling of sp3 C-H Bonds with sp2 and sp3 boronic acids using air as the oxidant.

Authors:  Dong-Hui Wang; Masayuki Wasa; Ramesh Giri; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2008-05-14       Impact factor: 15.419

9.  Catalytic direct acetoxylation of indoles.

Authors:  Ilga Mutule; Edgars Suna; Kristofer Olofsson; Benjamin Pelcman
Journal:  J Org Chem       Date:  2009-09-18       Impact factor: 4.354

10.  O-acetyl oximes as transformable directing groups for Pd-catalyzed C-H bond functionalization.

Authors:  Sharon R Neufeldt; Melanie S Sanford
Journal:  Org Lett       Date:  2010-02-05       Impact factor: 6.005

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  5 in total

1.  Surprisingly Facile C-H Activation in the Course of Oxime-Directed Catalytic Asymmetric Hydroboration.

Authors:  Nathan C Thacker; Veronika M Shoba; Andrew E Geis; James M Takacs
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2.  Enantio- and Diastereoswitchable C-H Arylation of Methylene Groups in Cycloalkanes.

Authors:  Michal S Andrä; Lukas Schifferer; Corina H Pollok; Christian Merten; Lukas J Gooßen; Jin-Quan Yu
Journal:  Chemistry       Date:  2019-05-27       Impact factor: 5.236

3.  Enantioselective palladium(0)-catalyzed intramolecular cyclopropane functionalization: access to dihydroquinolones, dihydroisoquinolones and the BMS-791325 ring system.

Authors:  J Pedroni; T Saget; P A Donets; N Cramer
Journal:  Chem Sci       Date:  2015-06-17       Impact factor: 9.825

4.  Copper-Catalyzed Enantioselective Hydrosilylation of gem-Difluorocyclopropenes Leading to a Stereochemical Study of the Silylated gem-Difluorocyclopropanes.

Authors:  Keisuke Sekine; Dai Akaishi; Kakeru Konagaya; Shigekazu Ito
Journal:  Chemistry       Date:  2022-05-02       Impact factor: 5.020

5.  Carboxylate-assisted C-H activation of phenylpyridines with copper, palladium and ruthenium: a mass spectrometry and DFT study.

Authors:  A Gray; A Tsybizova; J Roithova
Journal:  Chem Sci       Date:  2015-07-01       Impact factor: 9.825

  5 in total

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