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Literature DB >> 20625455

Solvent-dependent oxidative coupling of 1-aryl-1,3-dicarbonyls and styrene.

Brian M Casey¹, Cynthia A Eakin, Jingliang Jiao, Dhandapani V Sadasivam, Robert A Flowers.

Abstract

This report describes the scope and mechanism of the solvent-dependent, chemoselective oxidative coupling of 1-aryl-1,3-dicarbonyls with styrene using Ce(IV) reagents. Dihydrofuran derivatives are obtained when reactions are performed in methanol whereas alpha-tetralones can be selectively synthesized in acetonitrile and methylene chloride. Mechanistic studies are consistent with the rate of solvent-assisted deprotonation of a radical cation intermediate playing an integral role in the selective formation of products.

Entities: Chemical Species

Year: 2009 PMID： 20625455 PMCID： PMC2898135 DOI： 10.1016/j.tet.2009.06.118

Source DB: PubMed Journal: Tetrahedron ISSN： 0040-4020 Impact factor: 2.457

12 in total

1. Anti-inflammatory phloroglucinols and terpenoids from Garcinia subelliptica.

Authors: Jing-Ru Weng; Lo-Ti Tsao; Jih-Pyang Wang; Ru-Rong Wu; Chun-Nan Lin
Journal: J Nat Prod Date: 2004-11 Impact factor: 4.050

2. An efficient and general approach to beta-functionalized ketones.

Authors: Jingliang Jiao; Larry X Nguyen; Dennis R Patterson; Robert A Flowers
Journal: Org Lett Date: 2007-03-03 Impact factor: 6.005

3. Cerium(IV) ammonium nitrate--a versatile single-electron oxidant.

Authors: Vijay Nair; Ani Deepthi
Journal: Chem Rev Date: 2007-04-14 Impact factor: 60.622

4. Reactivity and acid-base behavior of ring-methoxylated arylalkanoic acid radical cations and radical zwitterions in aqueous solution. Influence of structural effects and pH on the benzylic C-H deprotonation pathway.

Authors: Massimo Bietti; Alberto Capone
Journal: J Org Chem Date: 2006-07-07 Impact factor: 4.354

10. Mechanistic studies of Ce(IV)-mediated oxidation of beta-dicarbonyls: solvent-dependent behavior of radical cation intermediates.

Authors: Jingliang Jiao; Yang Zhang; James J Devery; Luna Xu; Jennifer Deng; Robert A Flowers
Journal: J Org Chem Date: 2007-06-28 Impact factor: 4.354

1 in total

1. Mechanisms of Mn(OAc)(3)-based oxidative free-radical additions and cyclizations.

Authors: Barry B Snider
Journal: Tetrahedron Date: 2009-12-26 Impact factor: 2.457

1 in total

Solvent-dependent oxidative coupling of 1-aryl-1,3-dicarbonyls and styrene.

1. Anti-inflammatory phloroglucinols and terpenoids from Garcinia subelliptica.

2. An efficient and general approach to beta-functionalized ketones.

3. Cerium(IV) ammonium nitrate--a versatile single-electron oxidant.

4. Reactivity and acid-base behavior of ring-methoxylated arylalkanoic acid radical cations and radical zwitterions in aqueous solution. Influence of structural effects and pH on the benzylic C-H deprotonation pathway.

5. Spinonin, a novel glycoside from Ononis spinosa subsp. leiosperma.

6. Generation and absolute reactivity of an aryl enol radical cation in solution.

7. Solvent-dependent chemoselectivities in additions of beta-carbonyl imines to allyltrimethylsilane with CTAN.

8. One-pot, two-step, practical catalytic synthesis of 2,5-diformylfuran from fructose.

Review 9. Podophyllotoxin: distribution, sources, applications and new cytotoxic derivatives.

10. Mechanistic studies of Ce(IV)-mediated oxidation of beta-dicarbonyls: solvent-dependent behavior of radical cation intermediates.

1. Mechanisms of Mn(OAc)(3)-based oxidative free-radical additions and cyclizations.