Literature DB >> 24596034

Iron-catalyzed C(sp(2))-H and C(sp(3))-H arylation by triazole assistance.

Qing Gu1, Hamad H Al Mamari, Karolina Graczyk, Emelyne Diers, Lutz Ackermann.   

Abstract

Modular 1,2,3-triazoles enabled iron-catalyzed CH arylations with broad scope. The novel triazole-based bidentate auxiliary is easily accessible in a highly modular fashion and allowed for user-friendly iron-catalyzed C(sp(2) )H functionalizations of arenes and alkenes with excellent chemo- and diastereoselectivities. The versatile iron catalyst also proved applicable for challenging C(sp(3) )H functionalizations, and proceeds by an organometallic mode of action. The triazole-assisted CH activation strategy occurred under remarkably mild reaction conditions, and the auxiliary was easily removed in a traceless fashion. Intriguingly, the triazole group proved superior to previously used auxiliaries.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CH activation; chelation; iron; ruthenium; triazoles

Mesh:

Substances:

Year:  2014        PMID: 24596034     DOI: 10.1002/anie.201311024

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


  14 in total

1.  Bidentate, monoanionic auxiliary-directed functionalization of carbon-hydrogen bonds.

Authors:  Olafs Daugulis; James Roane; Ly Dieu Tran
Journal:  Acc Chem Res       Date:  2015-03-10       Impact factor: 22.384

2.  Palladium-Catalyzed Pyrazole-Directed sp3 C-H Bond Arylation for the Synthesis of β-Phenethylamines.

Authors:  Nurbey Gulia; Olafs Daugulis
Journal:  Angew Chem Int Ed Engl       Date:  2017-02-24       Impact factor: 15.336

Review 3.  Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp3)-H Bonds.

Authors:  Bin Liu; Andrew M Romine; Camille Z Rubel; Keary M Engle; Bing-Feng Shi
Journal:  Chem Rev       Date:  2021-10-29       Impact factor: 60.622

4.  Mechanistic Insights into Iron-Catalyzed C-H Bond Activation and C-C Coupling.

Authors:  Samantha M Brewer; Timothy M Schwartz; Magy A Mekhail; Lara S Turan; Timothy J Prior; Timothy J Hubin; Benjamin G Janesko; Kayla N Green
Journal:  Organometallics       Date:  2021-07-20       Impact factor: 3.837

5.  Additive and Counterion Effects in Iron-Catalyzed Reactions Relevant to C-C Bond Formation.

Authors:  Nikki J Bakas; Michael L Neidig
Journal:  ACS Catal       Date:  2021-06-29       Impact factor: 13.700

6.  1-Aminopyridinium Ylides as Monodentate Directing Groups for sp3 C-H Bond Functionalization.

Authors:  Ky Khac Anh Le; Hanh Nguyen; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2019-09-06       Impact factor: 15.419

Review 7.  A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

Authors:  Carlo Sambiagio; David Schönbauer; Remi Blieck; Toan Dao-Huy; Gerit Pototschnig; Patricia Schaaf; Thomas Wiesinger; Muhammad Farooq Zia; Joanna Wencel-Delord; Tatiana Besset; Bert U W Maes; Michael Schnürch
Journal:  Chem Soc Rev       Date:  2018-08-28       Impact factor: 54.564

8.  Palladium-Catalyzed Directed C(sp3)-H Arylation of Saturated Heterocycles at C-3 Using a Concise Optimization Approach.

Authors:  Dominic P Affron; James A Bull
Journal:  European J Org Chem       Date:  2015-11-27

Review 9.  Iron-Catalyzed C-H Functionalizations under Triazole-Assistance.

Authors:  Matteo Lanzi; Gianpiero Cera
Journal:  Molecules       Date:  2020-04-15       Impact factor: 4.411

10.  Experimental and computational studies of the mechanism of iron-catalysed C-H activation/functionalisation with allyl electrophiles.

Authors:  Joshua C DeMuth; Zhihui Song; Stephanie H Carpenter; Theresa E Boddie; Aleksa Radović; Tessa M Baker; Osvaldo Gutierrez; Michael L Neidig
Journal:  Chem Sci       Date:  2021-06-17       Impact factor: 9.825

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