Literature DB >> 24379522

SNAr-Derived Decomposition By-products Involving Pentafluorophenyl Triazolium Carbenes.

Xiaodan Zhao1, Garrett S Glover1, Kevin M Oberg1, Derek M Dalton1, Tomislav Rovis1.   

Abstract

Pentafluorophenyl triazolium carbenes, widely used in NHC-catalysis, can decompose by several mechanisms. Under high concentration conditions, the azolium may undergo a pentafluorophenyl exchange by a proposed SNAr mechanism to give an inactive salt. In the presence of appropriate substrates, cyclization on the ortho-position of the arene can occur, also by SNAr. These adducts provide a potential pathway for catalyst decomposition and serve as a caveat to the development of new reactions and catalysts.

Entities:  

Keywords:  Pentafluorophenyl N-heterocyclic carbene; decomposition; inner salt; spirocyclic oxindole

Year:  2013        PMID： 24379522      PMCID： PMC3873771          DOI： 10.1055/s-0033-1338842

Source DB:  PubMed          Journal:  Synlett        ISSN： 0936-5214            Impact factor:   2.454


  27 in total

1.  N-heterocyclic carbene (NHC)-catalyzed highly diastereo- and enantioselective oxo-Diels-Alder reactions for synthesis of fused pyrano[2,3-b]indoles.

Authors:  Limin Yang; Fei Wang; Pei Juan Chua; Yunbo Lv; Liang-Jun Zhong; Guofu Zhong
Journal:  Org Lett       Date:  2012-05-18       Impact factor: 6.005

2.  Enantioselective N-heterocyclic carbene-catalyzed Michael addition to α,β-unsaturated aldehydes by redox oxidation.

Authors:  Zi-Qiang Rong; Min-Qiang Jia; Shu-Li You
Journal:  Org Lett       Date:  2011-07-06       Impact factor: 6.005

3.  Enantioselective formation of substituted 3,4-dihydrocoumarins by a multicatalytic one-pot process.

Authors:  Christian Borch Jacobsen; Łukasz Albrecht; Jonas Udmark; Karl Anker Jørgensen
Journal:  Org Lett       Date:  2012-10-17       Impact factor: 6.005

4.  Catalytic asymmetric intermolecular Stetter reaction of enals with nitroalkenes: enhancement of catalytic efficiency through bifunctional additives.

Authors:  Daniel A DiRocco; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2011-06-16       Impact factor: 15.419

5.  Enantioselective activation of stable carboxylate esters as enolate equivalents via N-heterocyclic carbene catalysts.

Authors:  Lin Hao; Yu Du; Hui Lv; Xingkuan Chen; Huishen Jiang; Yaling Shao; Yonggui Robin Chi
Journal:  Org Lett       Date:  2012-04-09       Impact factor: 6.005

6.  N-heterocyclic carbene and Brønsted acid cooperative catalysis: asymmetric synthesis of trans-γ-lactams.

Authors:  Xiaodan Zhao; Daniel A DiRocco; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2011-07-25       Impact factor: 15.419

7.  N-heterocyclic carbene catalysed asymmetric cross-benzoin reactions of heteroaromatic aldehydes with trifluoromethyl ketones.

Authors:  Dieter Enders; André Grossmann; Jeanne Fronert; Gerhard Raabe
Journal:  Chem Commun (Camb)       Date:  2010-08-09       Impact factor: 6.222

8.  Asymmetric synthesis of functionalized cyclopentanones via a multicatalytic secondary amine/N-heterocyclic carbene catalyzed cascade sequence.

Authors:  Stephen P Lathrop; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2009-09-30       Impact factor: 15.419

9.  Catalytic asymmetric intermolecular Stetter reaction of glyoxamides with alkylidenemalonates.

Authors:  Qin Liu; Stéphane Perreault; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2008-10-04       Impact factor: 15.419

10.  Catalytic asymmetric intermolecular stetter reaction of heterocyclic aldehydes with nitroalkenes: backbone fluorination improves selectivity.

Authors:  Daniel A DiRocco; Kevin M Oberg; Derek M Dalton; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2009-08-12       Impact factor: 15.419
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  1 in total

1.  An Unexpected Inactivation of N-Heterocyclic Carbene Organic Catalyst by 1-Methylcyclopropylcarbaldehyde and 2,2,2-Trifluoroacetophenone.

Authors:  Yanling Chen; Jie Lv; Xuling Pan; Zhichao Jin
Journal:  Front Chem       Date:  2022-03-24       Impact factor: 5.221
  1 in total

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