Literature DB >> 19353605

Iridium catalysis for C-H bond arylation of heteroarenes with iodoarenes.

Benoît Join1, Takuya Yamamoto, Kenichiro Itami.   

Abstract

Efficient couplings using equimolar quantities of each coupling partner and multiple C-H bond arylation reactions are achieved with an Ir-based catalytic system for the C-H bond arylation of electron-rich heteroarenes with iodoarenes to construct extended pi-systems. The dramatic ligand effect on reaction efficiency leads to the discovery that Crabtree's catalyst (see scheme) is the optimal catalyst precursor.

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Year:  2009        PMID: 19353605     DOI: 10.1002/anie.200806358

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


  10 in total

1.  "Designer"-Surfactant-Enabled Cross-Couplings in Water at Room Temperature.

Authors:  Bruce H Lipshutz; Subir Ghorai
Journal:  Aldrichimica Acta       Date:  2012-01-01       Impact factor: 3.667

2.  Scope of the two-step, one-pot palladium-catalyzed borylation/Suzuki cross-coupling reaction utilizing bis-boronic acid.

Authors:  Gary A Molander; Sarah L J Trice; Steven M Kennedy
Journal:  J Org Chem       Date:  2012-09-20       Impact factor: 4.354

3.  Transition-Metal-Free C3 Arylation of Indoles with Aryl Halides.

Authors:  Ji Chen; Jimmy Wu
Journal:  Angew Chem Int Ed Engl       Date:  2017-03-03       Impact factor: 15.336

4.  Direct prenylation of aromatic and alpha,beta-unsaturated carboxamides via iridium-catalyzed C-H oxidative addition-allene insertion.

Authors:  Yong Jian Zhang; Eduardas Skucas; Michael J Krische
Journal:  Org Lett       Date:  2009-09-17       Impact factor: 6.005

5.  Tuning reactivity and site selectivity of simple arenes in C-H activation: ortho-arylation of anisoles via arene-metal π-complexation.

Authors:  Paolo Ricci; Katrina Krämer; Igor Larrosa
Journal:  J Am Chem Soc       Date:  2014-12-16       Impact factor: 15.419

6.  Ag(I)-C-H Activation Enables Near-Room-Temperature Direct α-Arylation of Benzo[ b]thiophenes.

Authors:  Chiara Colletto; Adyasha Panigrahi; Jaime Fernández-Casado; Igor Larrosa
Journal:  J Am Chem Soc       Date:  2018-07-23       Impact factor: 15.419

7.  Small organic molecules with tailored structures: initiators in the transition-metal-free C-H arylation of unactivated arenes.

Authors:  Zhenghui Liu; Peng Wang; Yu Chen; Zhenzhong Yan; Suqing Chen; Wenjun Chen; Tiancheng Mu
Journal:  RSC Adv       Date:  2020-04-09       Impact factor: 4.036

8.  C-H arylation and alkenylation of imidazoles by nickel catalysis: solvent-accelerated imidazole C-H activation.

Authors:  Kei Muto; Taito Hatakeyama; Junichiro Yamaguchi; Kenichiro Itami
Journal:  Chem Sci       Date:  2015-09-08       Impact factor: 9.825

9.  Catalytic Au(i)/Au(iii) arylation with the hemilabile MeDalphos ligand: unusual selectivity for electron-rich iodoarenes and efficient application to indoles.

Authors:  Jessica Rodriguez; Abdallah Zeineddine; E Daiann Sosa Carrizo; Karinne Miqueu; Nathalie Saffon-Merceron; Abderrahmane Amgoune; Didier Bourissou
Journal:  Chem Sci       Date:  2019-06-18       Impact factor: 9.825

10.  Catalyst-Controlled Regiodivergent C-H Alkynylation of Thiophenes*.

Authors:  Arup Mondal; Manuel van Gemmeren
Journal:  Angew Chem Int Ed Engl       Date:  2020-11-09       Impact factor: 16.823

  10 in total

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