邻碘苯甲酸（IBX）：pKa 及质子亲合性分析 - Suppr

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o-Iodoxybenzoic acid (IBX): pKa and proton-affinity analysis.

作者信息

Gallen Michael J, Goumont Régis, Clark Timothy, Terrier François, Williams Craig M

机构信息

School of Molecular and Microbial Sciences, University of Queensland, Brisbane, 4072, Queensland, Australia.

出版信息

Angew Chem Int Ed Engl. 2006 Apr 28;45(18):2929-34. doi: 10.1002/anie.200504156.

DOI:10.1002/anie.200504156

PMID:16566050

Abstract

摘要

相似文献

o-Iodoxybenzoic acid (IBX): pKa and proton-affinity analysis.

Angew Chem Int Ed Engl. 2006 Apr 28;45(18):2929-34. doi: 10.1002/anie.200504156.

In situ generation of o-iodoxybenzoic acid (IBX) and the catalytic use of it in oxidation reactions in the presence of Oxone as a co-oxidant.

Org Lett. 2005 Jul 7;7(14):2933-6. doi: 10.1021/ol050875o.

Experimental determination of the gas phase proton affinities of the conjugate base anions of 2-iodoxybenzoic acid (IBX) and 2-iodosobenzoic acid (IBA).

Org Biomol Chem. 2008 Jul 21;6(14):2530-3. doi: 10.1039/b803452d. Epub 2008 May 19.

New synthetic approach for the construction of multisubstituted 2-acyl furans by the IBX-mediated cascade oxidation/cyclization of cis-2-En-4-yn-1-ols (IBX=2-iodoxybenzoic acid).

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A new method for the synthesis of Z-enediones via IBX-mediated oxidative rearrangement of 2-alkynyl alcohol systems.

Chem Commun (Camb). 2006 Feb 21(7):764-6. doi: 10.1039/b515838a. Epub 2006 Jan 5.

Unexpected dehomologation of primary alcohols to one-carbon shorter carboxylic acids using o-iodoxybenzoic acid (IBX).

Chem Commun (Camb). 2014 Mar 14;50(21):2758-61. doi: 10.1039/c3cc49160a.

A mild, chemoselective oxidation of sulfides to sulfoxides using o-iodoxybenzoic acid and tetraethylammonium bromide as catalyst.

J Org Chem. 2003 Jun 27;68(13):5422-5. doi: 10.1021/jo034483b.

Iodoxybenzoic Acid (IBX) in Organic Synthesis: A Septennial Review.

Curr Org Synth. 2024;21(5):607-664. doi: 10.2174/0115701794263252230924074035.

IBX-Mediated Organic Transformations in Heterocyclic Chemistry-A Decade Update.

Front Chem. 2022 Feb 28;10:841751. doi: 10.3389/fchem.2022.841751. eCollection 2022.

2-Iodoxybenzoic acid--a simple oxidant with a dazzling array of potential applications.

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引用本文的文献

Iodoxybenzoic Acid (IBX) in Organic Synthesis: A Septennial Review.

Curr Org Synth. 2024;21(5):607-664. doi: 10.2174/0115701794263252230924074035.

Elucidating the mechanism of the Ley-Griffith (TPAP) alcohol oxidation.

Chem Sci. 2017 Dec 1;8(12):8435-8442. doi: 10.1039/c7sc04260d. Epub 2017 Oct 17.

Total Synthesis of (±)-Vibsanin E.

Aust J Chem. 2009;62(9):980-982. doi: 10.1071/CH09267.

Towards the Total Synthesis of 3-Hydroxyvibsanin E.

Synthesis (Stuttg). 2009 Sep 1;2009(17):2840-2846. doi: 10.1055/s-0029-1216912.

Chemistry of polyvalent iodine.

Chem Rev. 2008 Dec;108(12):5299-358. doi: 10.1021/cr800332c.

End game strategies towards the total synthesis of vibsanin E, 3-hydroxyvibsanin E, furanovibsanin A, and 3-O-methylfuranovibsanin A.

Beilstein J Org Chem. 2008;4:34. doi: 10.3762/bjoc.4.34. Epub 2008 Oct 8.

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相似文献

o-Iodoxybenzoic acid (IBX): pKa and proton-affinity analysis.

Angew Chem Int Ed Engl. 2006 Apr 28;45(18):2929-34. doi: 10.1002/anie.200504156.

In situ generation of o-iodoxybenzoic acid (IBX) and the catalytic use of it in oxidation reactions in the presence of Oxone as a co-oxidant.

Org Lett. 2005 Jul 7;7(14):2933-6. doi: 10.1021/ol050875o.

Experimental determination of the gas phase proton affinities of the conjugate base anions of 2-iodoxybenzoic acid (IBX) and 2-iodosobenzoic acid (IBA).

Org Biomol Chem. 2008 Jul 21;6(14):2530-3. doi: 10.1039/b803452d. Epub 2008 May 19.

New synthetic approach for the construction of multisubstituted 2-acyl furans by the IBX-mediated cascade oxidation/cyclization of cis-2-En-4-yn-1-ols (IBX=2-iodoxybenzoic acid).

Chemistry. 2008;14(31):9495-8. doi: 10.1002/chem.200801561.

A new method for the synthesis of Z-enediones via IBX-mediated oxidative rearrangement of 2-alkynyl alcohol systems.

Chem Commun (Camb). 2006 Feb 21(7):764-6. doi: 10.1039/b515838a. Epub 2006 Jan 5.

Unexpected dehomologation of primary alcohols to one-carbon shorter carboxylic acids using o-iodoxybenzoic acid (IBX).

Chem Commun (Camb). 2014 Mar 14;50(21):2758-61. doi: 10.1039/c3cc49160a.

A mild, chemoselective oxidation of sulfides to sulfoxides using o-iodoxybenzoic acid and tetraethylammonium bromide as catalyst.

J Org Chem. 2003 Jun 27;68(13):5422-5. doi: 10.1021/jo034483b.

Iodoxybenzoic Acid (IBX) in Organic Synthesis: A Septennial Review.

Curr Org Synth. 2024;21(5):607-664. doi: 10.2174/0115701794263252230924074035.

IBX-Mediated Organic Transformations in Heterocyclic Chemistry-A Decade Update.

Front Chem. 2022 Feb 28;10:841751. doi: 10.3389/fchem.2022.841751. eCollection 2022.

2-Iodoxybenzoic acid--a simple oxidant with a dazzling array of potential applications.

Angew Chem Int Ed Engl. 2011 Feb 11;50(7):1524-52. doi: 10.1002/anie.201000873. Epub 2011 Jan 26.

引用本文的文献

Iodoxybenzoic Acid (IBX) in Organic Synthesis: A Septennial Review.

Curr Org Synth. 2024;21(5):607-664. doi: 10.2174/0115701794263252230924074035.

Elucidating the mechanism of the Ley-Griffith (TPAP) alcohol oxidation.

Chem Sci. 2017 Dec 1;8(12):8435-8442. doi: 10.1039/c7sc04260d. Epub 2017 Oct 17.

Total Synthesis of (±)-Vibsanin E.

Aust J Chem. 2009;62(9):980-982. doi: 10.1071/CH09267.

Towards the Total Synthesis of 3-Hydroxyvibsanin E.

Synthesis (Stuttg). 2009 Sep 1;2009(17):2840-2846. doi: 10.1055/s-0029-1216912.

Chemistry of polyvalent iodine.

Chem Rev. 2008 Dec;108(12):5299-358. doi: 10.1021/cr800332c.

End game strategies towards the total synthesis of vibsanin E, 3-hydroxyvibsanin E, furanovibsanin A, and 3-O-methylfuranovibsanin A.

Beilstein J Org Chem. 2008;4:34. doi: 10.3762/bjoc.4.34. Epub 2008 Oct 8.

o-Iodoxybenzoic acid (IBX): pKa and proton-affinity analysis.

作者信息

Gallen Michael J, Goumont Régis, Clark Timothy, Terrier François, Williams Craig M

机构信息

School of Molecular and Microbial Sciences, University of Queensland, Brisbane, 4072, Queensland, Australia.

出版信息

Angew Chem Int Ed Engl. 2006 Apr 28;45(18):2929-34. doi: 10.1002/anie.200504156.

DOI:10.1002/anie.200504156

PMID:16566050

Abstract

摘要