Literature DB >> 24105995

Palladium-catalyzed through-space C(sp(3))-H and C(sp(2))-H bond activation by 1,4-palladium migration: efficient synthesis of [3,4]-fused oxindoles.

Tiffany Piou1, Ala Bunescu, Qian Wang, Luc Neuville, Jieping Zhu.   

Abstract

Palladium two step: Linear anilides were converted into the title compounds in good to excellent yields through a palladium-catalyzed domino carbopalladation/1,4-palladium shift sequence. The C(sp(3) )-H activation involves a seven-membered palladacycle, and is chemoselective in the presence of competitive C(sp(2) )H bonds. DMA=N,N-dimethylacetamide, OPiv=pivalate.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CH activation; chemoselectivity; heterocycles; palladium; synthetic methods

Mesh：

Substances：

Year:  2013        PMID： 24105995     DOI： 10.1002/anie.201306532

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


  11 in total

1.  Traceless Silylation of β-C(sp3)-H Bonds of Alcohols via Perfluorinated Acetals.

Authors:  Ala Bunescu; Trevor W Butcher; John F Hartwig
Journal:  J Am Chem Soc       Date:  2018-01-19       Impact factor: 15.419

2.  Ligand-enabled triple C-H activation reactions: one-pot synthesis of diverse 4-aryl-2-quinolinones from propionamides.

Authors:  Youqian Deng; Wei Gong; Jian He; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2014-05-14       Impact factor: 15.336

3.  Unexpected ortho-Heck Reaction under the Catellani Conditions.

Authors:  Alexander J Rago; Guangbin Dong
Journal:  Org Lett       Date:  2020-04-02       Impact factor: 6.005

4.  Iridium-catalyzed arylative cyclization of alkynones by 1,4-iridium migration.

Authors:  Benjamin M Partridge; Jorge Solana González; Hon Wai Lam
Journal:  Angew Chem Int Ed Engl       Date:  2014-05-19       Impact factor: 15.336

5.  Catalytic Asymmetric Reactions of 4-Substituted Indoles with Nitroethene: A Direct Entry to Ergot Alkaloid Structures.

Authors:  Simone Romanini; Emilio Galletti; Lorenzo Caruana; Andrea Mazzanti; Fahmi Himo; Stefano Santoro; Mariafrancesca Fochi; Luca Bernardi
Journal:  Chemistry       Date:  2015-10-21       Impact factor: 5.236

6.  Exploring the mechanism of the Pd-catalyzed spirocyclization reaction: a combined DFT and experimental study.

Authors:  Ivan Franzoni; Hyung Yoon; José-Antonio García-López; Amalia Isabel Poblador-Bahamonde; Mark Lautens
Journal:  Chem Sci       Date:  2017-12-08       Impact factor: 9.825

7.  Copper-catalyzed remote C(sp3)-H azidation and oxidative trifluoromethylation of benzohydrazides.

Authors:  Xu Bao; Qian Wang; Jieping Zhu
Journal:  Nat Commun       Date:  2019-02-15       Impact factor: 14.919

Review 8.  Modern Synthetic Methods for the Stereoselective Construction of 1,3-Dienes.

Authors:  Raquel G Soengas; Humberto Rodríguez-Solla
Journal:  Molecules       Date:  2021-01-06       Impact factor: 4.411

9.  Palladium-Catalyzed C(sp3 )-H Arylation of Primary Amines Using a Catalytic Alkyl Acetal to Form a Transient Directing Group.

Authors:  Sahra St John-Campbell; Alex K Ou; James A Bull
Journal:  Chemistry       Date:  2018-11-08       Impact factor: 5.236

10.  Synthesis of Spiroindenyl-2-Oxindoles through Palladium-Catalyzed Spirocyclization of 2-Bromoarylamides and Vinyl Bromides.

Authors:  Shuai Yang; Yanghui Zhang
Journal:  Molecules       Date:  2021-12-10       Impact factor: 4.411
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