Literature DB >> 25651006

Formal anti-carbopalladation reactions of non-activated alkynes: requirements, mechanistic insights, and applications.

Martin Pawliczek1, Tobias F Schneider, Christian Maass, Dietmar Stalke, Daniel B Werz.   

Abstract

Formal anti-carbopalladation reactions of CC triple bonds are uncommon, but highly useful transformations. Alkynes can be designed to give anti-carbopalladation products. Prerequisite is the exclusion of other reaction pathways to provoke the cis-trans isomerization of the syn-carbopalladation intermediate. Detailed mechanistic studies of this crucial step by experimental and computational means were performed. Application of an intramolecular version for the synthesis of oligocyclic compounds and substituted dibenzofurans is also described.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  anti-carbopalladation; domino reaction; palladium; reaction mechanisms

Year:  2015        PMID： 25651006     DOI： 10.1002/anie.201411210

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  7 in total

1.  Mapping Ambiphile Reactivity Trends in the Anti-(Hetero)annulation of Non-Conjugated Alkenes via PdII /PdIV Catalysis.

Authors:  Hui-Qi Ni; Phillippa Cooper; Shouliang Yang; Fen Wang; Neal Sach; Pranali G Bedekar; Joyann S Donaldson; Michelle Tran-Dubé; Indrawan J McAlpine; Keary M Engle
Journal:  Angew Chem Int Ed Engl       Date:  2022-02-02       Impact factor: 15.336

2.  Mechanistic Studies of Pd(II)-Catalyzed E/Z Isomerization of Unactivated Alkenes: Evidence for a Monometallic Nucleopalladation Pathway.

Authors:  Rei Matsuura; Malkanthi K Karunananda; Mingyu Liu; Nhi Nguyen; Donna G Blackmond; Keary M Engle
Journal:  ACS Catal       Date:  2021-03-19       Impact factor: 13.084

3.  Cationic-palladium catalyzed regio- and stereoselective syn-1,2-dicarbofunctionalization of unsymmetrical internal alkynes.

Authors:  Shubham Dutta; Shashank Shandilya; Shengwen Yang; Manash Protim Gogoi; Vincent Gandon; Akhila K Sahoo
Journal:  Nat Commun       Date:  2022-03-16       Impact factor: 14.919

4.  Synthesis of Benzofused O- and N-Heterocycles through Cascade Carbopalladation/Cross-Alkylation of Alkynes Involving the C-C Cleavage of Cyclobutanols.

Authors:  Marta Pérez-Gómez; Piedad Herrera-Ramírez; Delia Bautista; Isabel Saura-Llamas; José-Antonio García-López
Journal:  Organometallics       Date:  2022-03-03       Impact factor: 3.876

5.  Palladium-Catalyzed trans-Hydroalkoxylation: Counterintuitive Use of an Aryl Iodide Additive to Promote C-H Bond Formation.

Authors:  Ashis Das; Luca Buzzetti; Mikus Puriņš; Jerome Waser
Journal:  ACS Catal       Date:  2022-06-13       Impact factor: 13.700

Review 6.  Nickel-Catalyzed Arylative Cyclizations of Alkyne- and Allene-Tethered Electrophiles using Arylboron Reagents.

Authors:  Simone M Gillbard; Hon Wai Lam
Journal:  Chemistry       Date:  2022-01-27       Impact factor: 5.020

Review 7.  Recent Advances in Construction of Polycyclic Natural Product Scaffolds via One-Pot Reactions Involving Alkyne Annulation.

Authors:  Liyao Zheng; Ruimao Hua
Journal:  Front Chem       Date:  2020-10-15       Impact factor: 5.221
  7 in total

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