Literature DB >> 16928088

Discovery of a practical direct O2-coupled Wacker oxidation with Pd[(-)-sparteine]Cl2.

Candace N Cornell1, Matthew S Sigman.   

Abstract

The discovery of a direct O2-coupled Wacker oxidation with use of balloon pressure of O2 and low catalyst loading is described. Use of (-)-sparteine as a ligand on Pd prevents olefin isomerization and leads to selective formation of methyl ketones from terminal olefins in good yields. Oxidation of enantiomerically enriched substrates is reported with no observed racemization.

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Year:  2006        PMID: 16928088     DOI: 10.1021/ol061662h

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  10 in total

1.  Peroxide-Mediated Wacker Oxidations for Organic Synthesis.

Authors:  Brian W Michel; Matthew S Sigman
Journal:  Aldrichimica Acta       Date:  2011       Impact factor: 3.667

2.  Experimental and computational study of a direct O2-coupled Wacker oxidation: water dependence in the absence of Cu salts.

Authors:  Brian J Anderson; John A Keith; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2010-09-01       Impact factor: 15.419

3.  Imparting catalyst control upon classical palladium-catalyzed alkenyl C-H bond functionalization reactions.

Authors:  Matthew S Sigman; Erik W Werner
Journal:  Acc Chem Res       Date:  2011-11-23       Impact factor: 22.384

4.  Regiocontrolled Wacker Oxidation of Cinnamyl Azides.

Authors:  Angela S Carlson; Cristian Calcanas; Ryan M Brunner; Joseph J Topczewski
Journal:  Org Lett       Date:  2018-03-02       Impact factor: 6.005

5.  Recent advancements and challenges of palladium(II)-catalyzed oxidation reactions with molecular oxygen as the sole oxidant.

Authors:  Keith M Gligorich; Matthew S Sigman
Journal:  Chem Commun (Camb)       Date:  2009-05-14       Impact factor: 6.222

6.  On the mechanism of the palladium-catalyzed tert-butylhydroperoxide-mediated Wacker-type oxidation of alkenes using quinoline-2-oxazoline ligands.

Authors:  Brian W Michel; Laura D Steffens; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2011-05-09       Impact factor: 15.419

7.  Catalyst-controlled Wacker-type oxidation of protected allylic amines.

Authors:  Brian W Michel; Jessica R McCombs; Andrea Winkler; Matthew S Sigman
Journal:  Angew Chem Int Ed Engl       Date:  2010-09-24       Impact factor: 15.336

8.  A general and efficient catalyst system for a Wacker-type oxidation using TBHP as the terminal oxidant: application to classically challenging substrates.

Authors:  Brian W Michel; Andrew M Camelio; Candace N Cornell; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2009-05-06       Impact factor: 15.419

9.  A new approach to carbon-carbon bond formation: Development of aerobic Pd-catalyzed reductive coupling reactions of organometallic reagents and styrenes.

Authors:  Keith M Gligorich; Yasumasa Iwai; Sarah A Cummings; Matthew S Sigman
Journal:  Tetrahedron       Date:  2009-06-27       Impact factor: 2.457

10.  Trace Ethylene Sensing via Wacker Oxidation.

Authors:  Darryl Fong; Shao-Xiong Luo; Rafaela S Andre; Timothy M Swager
Journal:  ACS Cent Sci       Date:  2020-03-18       Impact factor: 14.553

  10 in total

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