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Literature DB >> 22432641

Allylic carbon-carbon double bond directed Pd-catalyzed oxidative ortho-olefination of arenes.

Parthasarathy Gandeepan¹, Chien-Hong Cheng.

Abstract

Pd-catalyzed selective ortho-olefination of arenes assisted by an allylic C-C double bond at room temperature using O(2) as a terminal oxidant is described. A possible mechanism involving the initial coordination of allylic C═C bond to Pd followed by selective o-C-H bond metalation is proposed.

Entities: Chemical

Year: 2012 PMID： 22432641 DOI： 10.1021/ja300168m

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

11 in total

1. Ligand-Accelerated ortho-C-H Olefination of Phenylacetic Acids.

Authors: Keary M Engle; Navid Dastbaravardeh; Peter S Thuy-Boun; Dong-Hui Wang; Aaron C Sather; Jin-Quan Yu
Journal: Organic Synth Date: 2015-03-12

2. Ether-directed ortho-C-H olefination with a palladium(II)/monoprotected amino acid catalyst.

Authors: Gang Li; Dasheng Leow; Li Wan; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2012-12-13 Impact factor: 15.336

3. Pd-Catalyzed Acyl C-O Bond Activation for Selective Ring-Opening of α-Methylene-β-lactones with Amines.

Authors: Christian A Malapit; Donald R Caldwell; Nicole Sassu; Samuel Milbin; Amy R Howell
Journal: Org Lett Date: 2017-04-04 Impact factor: 6.005

4. Copper-catalyzed regioselective ortho C-H cyanation of vinylarenes.

Authors: Yang Yang; Stephen L Buchwald
Journal: Angew Chem Int Ed Engl Date: 2014-05-06 Impact factor: 15.336

5. Palladium-catalyzed allylic cross-coupling reactions of primary and secondary homoallylic electrophiles.

Authors: Benjamin J Stokes; Susanne M Opra; Matthew S Sigman
Journal: J Am Chem Soc Date: 2012-07-06 Impact factor: 15.419

6. Computational Study of Rh-Catalyzed Carboacylation of Olefins: Ligand-Promoted Rhodacycle Isomerization Enables Regioselective C-C Bond Functionalization of Benzocyclobutenones.

Authors: Gang Lu; Cheng Fang; Tao Xu; Guangbin Dong; Peng Liu
Journal: J Am Chem Soc Date: 2015-06-19 Impact factor: 15.419

Allylic carbon-carbon double bond directed Pd-catalyzed oxidative ortho-olefination of arenes.

1. Ligand-Accelerated ortho-C-H Olefination of Phenylacetic Acids.

2. Ether-directed ortho-C-H olefination with a palladium(II)/monoprotected amino acid catalyst.

3. Pd-Catalyzed Acyl C-O Bond Activation for Selective Ring-Opening of α-Methylene-β-lactones with Amines.

4. Copper-catalyzed regioselective ortho C-H cyanation of vinylarenes.

5. Palladium-catalyzed allylic cross-coupling reactions of primary and secondary homoallylic electrophiles.

6. Computational Study of Rh-Catalyzed Carboacylation of Olefins: Ligand-Promoted Rhodacycle Isomerization Enables Regioselective C-C Bond Functionalization of Benzocyclobutenones.

7. Olefin-Directed Palladium-Catalyzed Regio- and Stereoselective Oxidative Arylation of Allenes.

8. Rh-Catalyzed Desymmetrization of α-Quaternary Centers by Isomerization-Hydroacylation.

9. Pd(ii)-catalyzed remote regiodivergent ortho- and meta-C-H functionalizations of phenylethylamines.

10. Rhodium-Catalyzed Electrooxidative C-H Olefination of Benzamides.