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Literature DB >> 25060365

Cobalt-catalyzed, aminoquinoline-directed C(sp²)-H bond alkenylation by alkynes.

Abstract

A method for cobalt-catalyzed, aminoquinoline- and picolinamide-directed C(sp(2))-H bond alkenylation by alkynes was developed. The method shows excellent functional-group tolerance and both internal and terminal alkynes are competent substrates for the coupling. The reaction employs a Co(OAc)2⋅4 H2O catalyst, Mn(OAc)2 co-catalyst, and oxygen (from air) as a terminal oxidant.

Entities: Chemical Gene Species

Keywords: CH activation; alkenes; alkynes; cobalt; cyclization

Mesh：

Substances：

Year: 2014 PMID： 25060365 PMCID： PMC4167400 DOI： 10.1002/anie.201404579

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

54 in total

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Authors: Pin-Sheng Lee; Takeshi Fujita; Naohiko Yoshikai
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3. Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon-hydrogen bonds.

Authors: Dmitry Shabashov; Olafs Daugulis
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Authors: Will R Gutekunst; Phil S Baran
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5. Pd-catalyzed cascade carbopalladation-annulation reaction of 3-(2-iodobenzyl)-indoles into fused 6/5/7/6- and 6/5/5/6- heterocyclic systems.

Authors: Natalia Chernyak; David Tilly; Zhou Li; Vladimir Gevorgyan
Journal: Chem Commun (Camb) Date: 2009-11-17 Impact factor: 6.222

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Authors: Amanda J Hickman; Melanie S Sanford
Journal: Nature Date: 2012-04-11 Impact factor: 49.962

Review 7. 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

8. 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

9. Copper-promoted sulfenylation of sp2 C-H bonds.

Authors: Ly Dieu Tran; Ilya Popov; Olafs Daugulis
Journal: J Am Chem Soc Date: 2012-10-29 Impact factor: 15.419

10. Copper-catalyzed, directing group-assisted fluorination of arene and heteroarene C-H bonds.

Authors: Thanh Truong; Kristine Klimovica; Olafs Daugulis
Journal: J Am Chem Soc Date: 2013-06-12 Impact factor: 15.419

29 in total

1. Cobalt-Catalyzed Coupling of Benzoic Acid C-H Bonds with Alkynes, Styrenes, and 1,3-Dienes.

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Journal: Angew Chem Int Ed Engl Date: 2018-01-10 Impact factor: 15.336

2. Aminoquinoline-directed, cobalt-catalyzed carbonylation of sulfonamide sp² C-H bonds.

Authors: Tung Thanh Nguyen; Liene Grigorjeva; Olafs Daugulis
Journal: Chem Commun (Camb) Date: 2017-05-04 Impact factor: 6.222

3. 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

4. Cobalt-promoted dimerization of aminoquinoline benzamides.

Authors: Liene Grigorjeva; Olafs Daugulis
Journal: Org Lett Date: 2015-02-17 Impact factor: 6.005

5. Cobalt(III)-Catalyzed C-H Bond Amidation with Isocyanates.

Authors: Joshua R Hummel; Jonathan A Ellman
Journal: Org Lett Date: 2015-05-06 Impact factor: 6.005

6. Highly Stereoselective Cobalt(III)-Catalyzed Three-Component C-H Bond Addition Cascade.

Authors: Jeffrey A Boerth; Joshua R Hummel; Jonathan A Ellman
Journal: Angew Chem Int Ed Engl Date: 2016-06-15 Impact factor: 15.336

7. Expeditious Synthesis of Isoquinolones and Isocoumarins with a Vinyl Borane as an Acetylene Equivalent.

Authors: Momar Toure; Saul Jaime-Figueroa; George M Burslem; Craig M Crews
Journal: European J Org Chem Date: 2016-07-26

8. Cobalt-Catalyzed, Aminoquinoline-Directed Functionalization of Phosphinic Amide sp² C-H Bonds.

Authors: Tung Thanh Nguyen; Liene Grigorjeva; Olafs Daugulis
Journal: ACS Catal Date: 2015-12-22 Impact factor: 13.084

9. Iridium-Catalyzed, Silyl-Directed, peri-Borylation of C-H Bonds in Fused Polycyclic Arenes and Heteroarenes.

Authors: Bo Su; John F Hartwig
Journal: Angew Chem Int Ed Engl Date: 2018-07-13 Impact factor: 15.336

10. RhIII-Catalyzed Synthesis of Isoquinolones and 2-Pyridones via Annulation of N-Methoxyamides and Nitroalkenes.

Authors: Tyler J Potter; Yuantao Li; Michael D Ward; Jonathan A Ellman
Journal: European J Org Chem Date: 2018-06-11