Literature DB >> 16706500

Aerobic intramolecular oxidative amination of alkenes catalyzed by NHC-coordinated palladium complexes.

Michelle M Rogers1, Johanna E Wendlandt, Ilia A Guzei, Shannon S Stahl.   

Abstract

[reaction: see text] Palladium(II) complexes bearing a single N-heterocyclic carbene ligand serve as effective catalysts for the aerobic oxidative cyclization of alkenes with pendant sulfonamides. The use of carboxylic acid cocatalysts (AcOH and PhCO(2)H) often leads to significant improvements in catalyst stability and product yield and enables catalytic turnover to be achieved with air, rather than pure oxygen gas, as the source of O(2).

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Year:  2006        PMID: 16706500     DOI: 10.1021/ol060327q

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


  8 in total

1.  Diazafluorenone-Promoted Oxidation Catalysis: Insights into the Role of Bidentate Ligands in Pd-Catalyzed Aerobic Aza-Wacker Reactions.

Authors:  Paul B White; Jonathan N Jaworski; Geyunjian Harry Zhu; Shannon S Stahl
Journal:  ACS Catal       Date:  2016-03-11       Impact factor: 13.084

Review 2.  Palladium(II)-catalyzed alkene functionalization via nucleopalladation: stereochemical pathways and enantioselective catalytic applications.

Authors:  Richard I McDonald; Guosheng Liu; Shannon S Stahl
Journal:  Chem Rev       Date:  2011-03-23       Impact factor: 60.622

3.  Mechanistic studies of Wacker-type intramolecular aerobic oxidative amination of alkenes catalyzed by Pd(OAc)2/pyridine.

Authors:  Xuan Ye; Guosheng Liu; Brian V Popp; Shannon S Stahl
Journal:  J Org Chem       Date:  2011-01-20       Impact factor: 4.354

4.  Synthesis of Indolines and Derivatives by Aza-Heck Cyclization.

Authors:  Feiyang Xu; Katerina M Korch; Donald A Watson
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-13       Impact factor: 15.336

5.  Stereoselective synthesis of cis-2,5-disubstituted pyrrolidines via Wacker-type aerobic oxidative cyclization of alkenes with tert-butanesulfinamide nucleophiles.

Authors:  Joanne E Redford; Richard I McDonald; Matthew L Rigsby; Joshua D Wiensch; Shannon S Stahl
Journal:  Org Lett       Date:  2012-02-21       Impact factor: 6.005

6.  Synthesis of Pd Complexes Bearing an Enantiomerically-Resolved Seven-Membered N-Heterocyclic Carbene Ligands and Initial Studies of their Use in Asymmetric Wacker-Type Oxidative Cyclization Reactions.

Authors:  Christopher C Scarborough; Ana Bergant; Graham T Sazama; Ilia A Guzei; Lara C Spencer; Shannon S Stahl
Journal:  Tetrahedron       Date:  2009-06-27       Impact factor: 2.457

7.  Synthesis and isolation of a stable, axially-chiral seven-membered N-heterocyclic carbene.

Authors:  Christopher C Scarborough; Ilia A Guzei; Shannon S Stahl
Journal:  Dalton Trans       Date:  2009-02-13       Impact factor: 4.390

8.  Mechanistic studies of Wacker-type amidocyclization of alkenes catalyzed by (IMes)Pd(TFA)2(H2O): kinetic and stereochemical implications of proton transfer.

Authors:  Xuan Ye; Paul B White; Shannon S Stahl
Journal:  J Org Chem       Date:  2012-11-30       Impact factor: 4.354

  8 in total

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