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Literature DB >> 21793534

Rhodium-catalyzed oxidative ortho-acylation of benzamides with aldehydes: direct functionalization of the sp2 C-H bond.

Jihye Park¹, Eonjeong Park, Aejin Kim, Youngil Lee, Ki-Whan Chi, Jong Hwan Kwak, Young Hoon Jung, In Su Kim.

Abstract

A rhodium-catalyzed oxidative acylation of benzamides with aryl aldehydes via direct sp(2) C-H bond cleavage is described. In the presence of [Cp*RhCl(2)](2), AgSbF(6), and silver carbonate as an oxidant, N,N-diethyl benzamides can be effectively carbonylated to yield ortho-acyl benzamides.

Entities: Chemical

Mesh：

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Year: 2011 PMID： 21793534 DOI： 10.1021/ol201729w

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

12 in total

1. Rhodium(iii)-catalyzed synthesis of phthalides by cascade addition and cyclization of benzimidates with aldehydes.

Authors: Yajing Lian; Robert G Bergman; Jonathan A Ellman
Journal: Chem Sci Date: 2012-08-02 Impact factor: 9.825

2. 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

3. Rhodium-catalyzed synthesis of branched amines by direct addition of benzamides to imines.

Authors: Kevin D Hesp; Robert G Bergman; Jonathan A Ellman
Journal: Org Lett Date: 2012-04-13 Impact factor: 6.005

4. Transition-Metal-Catalyzed C-H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds.

Authors: Joshua R Hummel; Jeffrey A Boerth; Jonathan A Ellman
Journal: Chem Rev Date: 2016-12-12 Impact factor: 60.622

5. Synthesis of 2-Acylphenol and Flavene Derivatives from the Ruthenium-Catalyzed Oxidative C-H Acylation of Phenols with Aldehydes.

Authors: Hanbin Lee; Chae S Yi
Journal: European J Org Chem Date: 2015-03

Rhodium-catalyzed oxidative ortho-acylation of benzamides with aldehydes: direct functionalization of the sp2 C-H bond.

1. Rhodium(iii)-catalyzed synthesis of phthalides by cascade addition and cyclization of benzimidates with aldehydes.

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

3. Rhodium-catalyzed synthesis of branched amines by direct addition of benzamides to imines.

4. Transition-Metal-Catalyzed C-H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds.

5. Synthesis of 2-Acylphenol and Flavene Derivatives from the Ruthenium-Catalyzed Oxidative C-H Acylation of Phenols with Aldehydes.

6. Mechanism of the rhodium(III)-catalyzed arylation of imines via C-H bond functionalization: inhibition by substrate.

7. Rh(III)-Catalyzed Aryl and Alkenyl C-H Bond Addition to Diverse Nitroalkenes.

8. Rhodium(III)-catalyzed alkenyl C-H bond functionalization: convergent synthesis of furans and pyrroles.

9. Rhodium(III)-catalyzed indazole synthesis by C-H bond functionalization and cyclative capture.

10. Cobalt(III)-catalyzed synthesis of indazoles and furans by C-H bond functionalization/addition/cyclization cascades.