Literature DB >> 20806051

Corrigendum to 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 nitrate esters 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:  

Year:  2010        PMID: 20806051      PMCID: PMC2928991          DOI: 10.1016/j.tet.2010.05.063

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

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

Authors:  S Kirmizigül; N Gören; S W Yang; G A Cordell; C Bozok-Johansson
Journal:  J Nat Prod       Date:  1997-04       Impact factor: 4.050

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

Authors:  Norman P Schepp
Journal:  J Org Chem       Date:  2004-07-23       Impact factor: 4.354

7.  Enantioselective organo-singly occupied molecular orbital catalysis: the carbo-oxidation of styrenes.

Authors:  Thomas H Graham; Casey M Jones; Nathan T Jui; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2008-12-10       Impact factor: 15.419

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

Authors:  Yang Zhang; Andrew J Raines; Robert A Flowers
Journal:  J Org Chem       Date:  2004-09-17       Impact factor: 4.354

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

Authors:  Gary A Halliday; Robert J Young; Vladimir V Grushin
Journal:  Org Lett       Date:  2003-05-29       Impact factor: 6.005

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

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