Literature DB >> 24356913

Towards ideal synthesis: alkenylation of aryl C-H bonds by a Fujiwara-Moritani reaction.

Lihong Zhou1, Wenjun Lu.   

Abstract

An overview of recent progress in the Fujiwara-Moritani reaction, which is the palladium-catalyzed oxidative coupling of arenes with olefins to afford alkenyl arenes, is described. It is emphasized that regioselectivity on aryl ortho- or meta-CH activation could be controlled very well in the presence of Pd, Rh, or Ru catalysts with the assistance of various chelation groups on aromatic rings in this coupling reaction. Catalytic alkenylation of aryl CH bonds from simple arenes is also discussed, especially from electron-deficient arenes. These advanced protocols would not only make the Fujiwara-Moritani reaction more useful and applicable in organic synthesis but also light the way for the further development of the functionalization of normal CH bonds.
Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CC bond formation; CH activation; Fujiwara-Moritani reaction; arenes; oxidative coupling

Year:  2013        PMID: 24356913     DOI: 10.1002/chem.201303670

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  13 in total

1.  Base-Assisted C-H Bond Cleavage in Cross-Coupling: Recent Insights into Mechanism, Speciation, and Cooperativity.

Authors:  Brad P Carrow; Jessica Sampson; Long Wang
Journal:  Isr J Chem       Date:  2019-12-13       Impact factor: 3.333

2.  Contrasteric coupling of allenes and tetrahydroisoquinolines by iron-catalysed allenic C(sp2)-H functionalisation.

Authors:  Yue Xia; Nicholas W Wade; Philip N Palermo; Yidong Wang; Yi-Ming Wang
Journal:  Chem Commun (Camb)       Date:  2021-12-09       Impact factor: 6.222

3.  Ligand switchable site selectivity in C-H alkenylation of thiophenes by turnover-limiting step control.

Authors:  Rebecca Evans; Jessica Sampson; Long Wang; Lukas Lückemeier; Brad P Carrow
Journal:  Chem Commun (Camb)       Date:  2021-09-09       Impact factor: 6.065

4.  Preparation of tetrasubstituted olefins using mono or double aerobic direct C-H functionalization strategies: importance of steric effects.

Authors:  Nicolas Gigant; François Quintin; Jan-E Bäckvall
Journal:  J Org Chem       Date:  2015-02-16       Impact factor: 4.354

5.  Mechanistic and Kinetic Studies of the Direct Alkylation of Benzylic Amines: A Formal C(sp3)-H Activation Proceeds Actually via a C(sp2)-H Activation Pathway.

Authors:  Robert Pollice; Navid Dastbaravardeh; Nada Marquise; Marko D Mihovilovic; Michael Schnürch
Journal:  ACS Catal       Date:  2014-12-08       Impact factor: 13.084

6.  Merging Visible Light Photoredox Catalysis with Metal Catalyzed C-H Activations: On the Role of Oxygen and Superoxide Ions as Oxidants.

Authors:  David C Fabry; Magnus Rueping
Journal:  Acc Chem Res       Date:  2016-08-24       Impact factor: 22.384

7.  Palladium-Catalyzed Dehydrogenative Coupling: An Efficient Synthetic Strategy for the Construction of the Quinoline Core.

Authors:  Asier Carral-Menoyo; Verónica Ortiz-de-Elguea; Mikel Martinez-Nunes; Nuria Sotomayor; Esther Lete
Journal:  Mar Drugs       Date:  2017-08-30       Impact factor: 5.118

8.  Cobalt-catalyzed directed C-H alkenylation of pivalophenone N-H imine with alkenyl phosphates.

Authors:  Wengang Xu; Naohiko Yoshikai
Journal:  Beilstein J Org Chem       Date:  2018-03-28       Impact factor: 2.883

9.  Pd(ii)-catalyzed remote regiodivergent ortho- and meta-C-H functionalizations of phenylethylamines.

Authors:  Shangda Li; Huafang Ji; Lei Cai; Gang Li
Journal:  Chem Sci       Date:  2015-06-25       Impact factor: 9.825

Review 10.  When metal-catalyzed C-H functionalization meets visible-light photocatalysis.

Authors:  Lucas Guillemard; Joanna Wencel-Delord
Journal:  Beilstein J Org Chem       Date:  2020-07-21       Impact factor: 2.883

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