Literature DB >> 17576481

Intramolecular aminopalladation of alkenes as a key step to pyrrolidines and related heterocycles.

Ana Minatti1, Kilian Muñiz.   

Abstract

Palladium catalysis for the intramolecular amination of alkenes is a powerful approach in heterocycle synthesis. The initial common step in this approach consists of an aminopalladation reaction. This tutorial review describes the synthesis of 2-amino alkyl-palladium compounds and renders special attention on the subsequent manipulation of the alkyl-palladium group. By carefully choosing the appropriate conditions, a wide variety of different heterocyclic structures are accessible which arise from reactions such as hydroamination, aza-Heck coupling, aminocarbonylation or oxidative processes such as aza-Wacker reaction and 1,2-difunctionalization.

Entities:  

Year:  2007        PMID: 17576481     DOI: 10.1039/b607474j

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  39 in total

1.  Palladium-catalyzed alkene carboamination reactions for the synthesis of substituted piperazines.

Authors:  Josephine S Nakhla; Danielle M Schultz; John P Wolfe
Journal:  Tetrahedron       Date:  2009-09-15       Impact factor: 2.457

2.  Reversible alkene insertion into the Pd-N bond of Pd(II)-sulfonamidates and implications for catalytic amidation reactions.

Authors:  Paul B White; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2011-10-31       Impact factor: 15.419

3.  Can Donor Ligands Make Pd(OAc)2 a Stronger Oxidant? Access to Elusive Palladium(II) Reduction Potentials and Effects of Ancillary Ligands via Palladium(II)/Hydroquinone Redox Equilibria.

Authors:  David L Bruns; Djamaladdin G Musaev; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2020-11-09       Impact factor: 15.419

4.  Driving Catalyst Reoxidation in Wacker Cyclizations with Acetal-Based Metal-Hydride Abstractors.

Authors:  Nikki A Cochrane; Maurice S Brookhart; Michel R Gagné
Journal:  Organometallics       Date:  2011-05-09       Impact factor: 3.876

5.  Synthesis of Secondary Unsaturated Lactams via an Aza-Heck Reaction.

Authors:  Scott A Shuler; Guoyin Yin; Sarah B Krause; Caroline M Vesper; Donald A Watson
Journal:  J Am Chem Soc       Date:  2016-10-18       Impact factor: 15.419

6.  Mechanistic Studies of Azaphilic versus Carbophilic Activation by Gold(I) in the Gold/Palladium Dual-Catalyzed Rearrangement of Alkenyl Vinyl Aziridines.

Authors:  Joshua J Hirner; Katrina E Roth; Yili Shi; Suzanne A Blum
Journal:  Organometallics       Date:  2012-10-08       Impact factor: 3.876

7.  Stereoselective Synthesis of Saturated Heterocycles via Pd-Catalyzed Alkene Carboetherification and Carboamination Reactions.

Authors:  John P Wolfe
Journal:  Synlett       Date:  2006-11-13       Impact factor: 2.454

8.  Reconciling the stereochemical course of nucleopalladation with the development of enantioselective wacker-type cyclizations.

Authors:  Adam B Weinstein; Shannon S Stahl
Journal:  Angew Chem Int Ed Engl       Date:  2012-10-16       Impact factor: 15.336

9.  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

10.  Methods for direct alkene diamination, new & old.

Authors:  Sam de Jong; Daniel G Nosal; Duncan J Wardrop
Journal:  Tetrahedron       Date:  2012-03-21       Impact factor: 2.457

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