Literature DB >> 33664525

Pd-Catalyzed C-C, C-N, and C-O Bond-Forming Difunctionalization Reactions of Alkenes Bearing Tethered Aryl/Alkenyl Triflates.

Derick R White1, Evan C Bornowski1, John P Wolfe1.   

Abstract

Over the past few years our group has described a new type of alkene difunctionalization reaction in which aryl or alkenyl triflates bearing tethered alkenes are coupled with various nucleophiles to afford carbocyclic products. The products are formed in moderate to good chemical yield, with generally high levels of stereoselectivity. Our progress to date in this area, which includes reactions of amine, alcohol, enolate, and indole nucleophiles, is described in this review.

Entities:  

Keywords:  Alkenes; Carbocycles; Cross Coupling; Heterocycles; Palladium

Year:  2020        PMID: 33664525      PMCID: PMC7929490          DOI: 10.1002/ijch.201900108

Source DB:  PubMed          Journal:  Isr J Chem        ISSN: 0021-2148            Impact factor:   3.333


  45 in total

1.  Intermolecular migratory insertion of unactivated olefins into palladium-nitrogen bonds. Steric and electronic effects on the rate of migratory insertion.

Authors:  Patrick S Hanley; John F Hartwig
Journal:  J Am Chem Soc       Date:  2011-09-08       Impact factor: 15.419

2.  Synthesis of Cyclic Guanidines Bearing N-Arylsulfonyl and N-Cyano Protecting Groups via Pd-Catalyzed Alkene Carboamination Reactions.

Authors:  Luke J Peterson; Jingyi Luo; John P Wolfe
Journal:  Org Lett       Date:  2017-05-23       Impact factor: 6.005

3.  Intramolecular alkene aminopalladation reactions of (dppf)Pd(Ar)[N(Ar(1))(CH(2))(3)CH=CH(2)] complexes. insertion of unactivated alkenes into Pd-N bonds.

Authors:  Joshua D Neukom; Nicholas S Perch; John P Wolfe
Journal:  J Am Chem Soc       Date:  2010-05-12       Impact factor: 15.419

4.  Migratory insertion of alkenes into metal-oxygen and metal-nitrogen bonds.

Authors:  Patrick S Hanley; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-05       Impact factor: 15.336

5.  Synthesis of enantiomerically enriched imidazolidin-2-ones through asymmetric palladium-catalyzed alkene carboamination reactions.

Authors:  Brett A Hopkins; John P Wolfe
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-31       Impact factor: 15.336

6.  Palladium-Catalyzed Alkene Carboamination Reactions of Electron-Poor Nitrogen Nucleophiles.

Authors:  Luke J Peterson; John P Wolfe
Journal:  Adv Synth Catal       Date:  2015-07-14       Impact factor: 5.837

7.  Stereocontrolled Synthesis of Amino-Substituted Carbocycles by Pd-Catalyzed Alkene Carboamination Reactions.

Authors:  Derick R White; John P Wolfe
Journal:  Chemistry       Date:  2017-04-03       Impact factor: 5.236

Review 8.  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

9.  Desymmetrization of meso-2,5-diallylpyrrolidinyl ureas through asymmetric palladium-catalyzed carboamination: stereocontrolled synthesis of bicyclic ureas.

Authors:  Nicholas R Babij; John P Wolfe
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-03       Impact factor: 15.336

Review 10.  Biaryl phosphane ligands in palladium-catalyzed amination.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

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