Literature DB >> 28657674

A Convergent Synthesis of Functionalized Alkenyl Halides through Cobalt(III)-Catalyzed Three-Component C-H Bond Addition.

Jeffrey A Boerth1, Jonathan A Ellman1.   

Abstract

A CoIII -catalyzed three-component coupling of C(sp2 )-H bonds, alkynes, and halogenating agents to give alkenyl halides is reported. This transformation proceeds with high regio- and diastereoselectivity, and is effective for a broad range of aryl and alkyl terminal alkynes. Diverse C-H bond partners also exhibit good reactivity for a range of heteroaryl and aryl systems as well as synthetically useful secondary and tertiary amide, urea, and pyrazole directing groups. This multicomponent transformation is also compatible with allenes in place of alkynes to furnish tetrasubstituted alkenyl halides, showcasing the first halo-arylation of allenes.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−H activation; alkynes; allenes; homogeneous catalysis; multicomponent reactions

Mesh：

Substances：

Year:  2017        PMID： 28657674      PMCID： PMC5568819          DOI： 10.1002/anie.201705817

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


  41 in total

1.  From C(sp2)-H to C(sp3)-H: systematic studies on transition metal-catalyzed oxidative C-C formation.

Authors:  Bi-Jie Li; Zhang-Jie Shi
Journal:  Chem Soc Rev       Date:  2012-07-10       Impact factor: 54.564

Review 2.  Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis.

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Journal:  Chem Rev       Date:  2008-08       Impact factor: 60.622

Review 3.  Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

Authors:  Ranjan Jana; Tejas P Pathak; Matthew S Sigman
Journal:  Chem Rev       Date:  2011-02-14       Impact factor: 60.622

4.  Ruthenium(II)-catalyzed C-H bond activation and functionalization.

Authors:  Percia Beatrice Arockiam; Christian Bruneau; Pierre H Dixneuf
Journal:  Chem Rev       Date:  2012-08-31       Impact factor: 60.622

5.  Mild metal-catalyzed C-H activation: examples and concepts.

Authors:  T Gensch; M N Hopkinson; F Glorius; J Wencel-Delord
Journal:  Chem Soc Rev       Date:  2016-04-13       Impact factor: 54.564

6.  Cobalt-Catalyzed sp(2) -C-H Activation: Intermolecular Heterocyclization with Allenes at Room Temperature.

Authors:  Neetipalli Thrimurtulu; Arnab Dey; Debabrata Maiti; Chandra M R Volla
Journal:  Angew Chem Int Ed Engl       Date:  2016-09-01       Impact factor: 15.336

7.  Stereoselective Synthesis of Exocyclic Tetrasubstituted Vinyl Halides via Ru-Catalyzed Halotropic Cycloisomerization of 1,6-Haloenynes.

Authors:  Barry M Trost; Christopher A Kalnmals
Journal:  Org Lett       Date:  2017-04-24       Impact factor: 6.005

Review 8.  C-H bond functionalization: emerging synthetic tools for natural products and pharmaceuticals.

Authors:  Junichiro Yamaguchi; Atsushi D Yamaguchi; Kenichiro Itami
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-06       Impact factor: 15.336

9.  Mn-catalyzed aromatic C-H alkenylation with terminal alkynes.

Authors:  Bingwei Zhou; Hui Chen; Congyang Wang
Journal:  J Am Chem Soc       Date:  2013-01-15       Impact factor: 15.419

10.  Rh(III)-Catalyzed Diastereoselective C-H Bond Addition/Cyclization Cascade of Enone Tethered Aldehydes.

Authors:  Jeffrey A Boerth; Jonathan A Ellman
Journal:  Chem Sci       Date:  2015-12-01       Impact factor: 9.825
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  8 in total

1.  Cobalt(III)-Catalyzed Diastereoselective Three-Component C-H Bond Addition to Butadiene and Activated Ketones.

Authors:  Zican Shen; Chen Li; Brandon Q Mercado; Jonathan A Ellman
Journal:  Synthesis (Stuttg)       Date:  2019-11-07       Impact factor: 3.157

2.  Synthesis of Homoallylic Alcohols with Acyclic Quaternary Centers through CoIII -Catalyzed Three-Component C-H Bond Addition to Internally Substituted Dienes and Carbonyls.

Authors:  Sun Dongbang; Zican Shen; Jonathan A Ellman
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-01       Impact factor: 15.336

Review 3.  C-H bond activation and sequential addition to two different coupling partners: a versatile approach to molecular complexity.

Authors:  Daniel S Brandes; Jonathan A Ellman
Journal:  Chem Soc Rev       Date:  2022-08-01       Impact factor: 60.615

4.  Stereoselective Synthesis of Allenyl Alcohols by Cobalt(III)-Catalyzed Sequential C-H Bond Addition to 1,3-Enynes and Aldehydes.

Authors:  Chaofan Xu; Joseph P Tassone; Brandon Q Mercado; Jonathan A Ellman
Journal:  Angew Chem Int Ed Engl       Date:  2022-04-29       Impact factor: 16.823

5.  Three-Component Friedel-Crafts Transformations: Synthesis of Alkyl and Alkenyl Trifluoromethyl Sulfides and Alkenyl Iodides.

Authors:  Duc Chu; Jonathan A Ellman
Journal:  Org Lett       Date:  2022-04-08       Impact factor: 6.072

Review 6.  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

7.  Selective and synergistic cobalt(III)-catalyzed three-component C-H bond addition to dienes and aldehydes.

Authors:  Jeffrey A Boerth; Soham Maity; Sarah K Williams; Brandon Q Mercado; Jonathan A Ellman
Journal:  Nat Catal       Date:  2018

8.  Synthesis of Nitrile Bearing Acyclic Quaternary Centers through Co(III)-Catalyzed Sequential C-H Bond Addition to Dienes and N-Cyanosuccinimide.

Authors:  Sun Dongbang; Jonathan A Ellman
Journal:  Angew Chem Int Ed Engl       Date:  2020-11-23       Impact factor: 15.336
  8 in total

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