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Literature DB >> 16568995

DDQ-mediated direct cross-dehydrogenative-coupling (CDC) between benzyl ethers and simple ketones.

Abstract

A direct Cross-Dehydrogenative-Coupling (CDC) between benzyl ethers and simple ketones was developed without using any metal catalyst. By using DDQ, various benzyl ethers and simples ketones were coupled together directly to form beta-alkoxyl ketones efficiently. A mechanism in which the DDQ serves the double roles of an oxidizing agent and an organomediator was proposed.

Entities: Chemical

Year: 2006 PMID： 16568995 DOI： 10.1021/ja060050p

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

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Cited

24 in total

1. Enantioselective copper-catalyzed alkynylation of benzopyranyl oxocarbenium ions.

Authors: Harathi D Srinivas; Prantik Maity; Glenn P A Yap; Mary P Watson
Journal: J Org Chem Date: 2015-04-07 Impact factor: 4.354

2. Efficient domino approaches to multifunctionalized fused pyrroles and dibenzo[b,e][1,4]diazepin-1-ones.

Authors: Bo Jiang; Qiu-Yun Li; Hao Zhang; Shu-Jiang Tu; Suresh Pindi; Guigen Li
Journal: Org Lett Date: 2012-01-19 Impact factor: 6.005

3. Copper-catalyzed enantioselective additions to oxocarbenium ions: alkynylation of isochroman acetals.

Authors: Prantik Maity; Harathi D Srinivas; Mary P Watson
Journal: J Am Chem Soc Date: 2011-10-11 Impact factor: 15.419

4. A multi-component domino reaction for the direct access to polyfunctionalized indoles via intermolecular allylic esterification and indolation.

Authors: Bo Jiang; Mian-Shuai Yi; Feng Shi; Shu-Jiang Tu; Suresh Pindi; Patrick McDowell; Guigen Li
Journal: Chem Commun (Camb) Date: 2011-10-31 Impact factor: 6.222

DDQ-mediated direct cross-dehydrogenative-coupling (CDC) between benzyl ethers and simple ketones.

1. Enantioselective copper-catalyzed alkynylation of benzopyranyl oxocarbenium ions.

2. Efficient domino approaches to multifunctionalized fused pyrroles and dibenzo[b,e][1,4]diazepin-1-ones.

3. Copper-catalyzed enantioselective additions to oxocarbenium ions: alkynylation of isochroman acetals.

4. A multi-component domino reaction for the direct access to polyfunctionalized indoles via intermolecular allylic esterification and indolation.

5. 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone-catalyzed reactions employing MnO2 as a stoichiometric oxidant.

6. Aromatic cations from oxidative carbon-hydrogen bond cleavage in bimolecular carbon-carbon bond forming reactions.

7. Oxidative carbocation formation in macrocycles: synthesis of the neopeltolide macrocycle.

8. Bimolecular Coupling Reactions through Oxidatively Generated Aromatic Cations: Scope and Stereocontrol.

Review 9. Quinone-Catalyzed Selective Oxidation of Organic Molecules.

10. Asymmetric Total Syntheses of Di- and Sesquiterpenoids by Catalytic C-C Activation of Cyclopentanones.