Literature DB >> 29106419

XtalFluor-E® mediated proto-functionalization of N-vinyl amides: access to N-acetyl N,O-acetals.

Y Yi1, H Gholami, M G Morrow, B Borhan.   

Abstract

XtalFluor-E® has been extensively used in a broad range of reactions in the past few years. Here we report its use with protic nucleophiles in a catalytic manner for the in situ generation of protons that lead to the proto-functionalization of activated olefins. Utilizing the latter protocol, proto etherification of enamides gives rise to N,O-acetals in nearly quantitative yields.

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Year:  2017        PMID： 29106419      PMCID： PMC5746421          DOI： 10.1039/c7ob02283b

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  21 in total

1.  A novel and selective fluoride opening of aziridines by XtalFluor-E. synthesis of fluorinated diamino acid derivatives.

Authors:  Melinda Nonn; Loránd Kiss; Matti Haukka; Santos Fustero; Ferenc Fülöp
Journal:  Org Lett       Date:  2015-02-16       Impact factor: 6.005

2.  PyFluor: A Low-Cost, Stable, and Selective Deoxyfluorination Reagent.

Authors:  Matthew K Nielsen; Christian R Ugaz; Wenping Li; Abigail G Doyle
Journal:  J Am Chem Soc       Date:  2015-07-21       Impact factor: 15.419

3.  A doubly axially chiral phosphoric acid catalyst for the asymmetric tandem oxyfluorination of enamides.

Authors:  Takashi Honjo; Robert J Phipps; Vivek Rauniyar; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-29       Impact factor: 15.336

4.  Good partnership between sulfur and fluorine: sulfur-based fluorination and fluoroalkylation reagents for organic synthesis.

Authors:  Chuanfa Ni; Mingyou Hu; Jinbo Hu
Journal:  Chem Rev       Date:  2014-08-21       Impact factor: 60.622

5.  Access to optically active 3-azido- and 3-aminopiperidine derivatives by enantioselective ring expansion of prolinols.

Authors:  Anne Cochi; Domingo Gomez Pardo; Janine Cossy
Journal:  Org Lett       Date:  2011-07-27       Impact factor: 6.005

Review 6.  Catalytic, asymmetric halofunctionalization of alkenes--a critical perspective.

Authors:  Scott E Denmark; William E Kuester; Matthew T Burk
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-25       Impact factor: 15.336

7.  Hydroamination and hydroalkoxylation catalyzed by triflic acid. Parallels to reactions initiated with metal triflates.

Authors:  Devon C Rosenfeld; Shashank Shekhar; Akihiro Takemiya; Masaru Utsunomiya; John F Hartwig
Journal:  Org Lett       Date:  2006-09-14       Impact factor: 6.005

8.  In situ activation of benzyl alcohols with XtalFluor-E: formation of 1,1-diarylmethanes and 1,1,1-triarylmethanes through Friedel-Crafts benzylation.

Authors:  Justine Desroches; Pier Alexandre Champagne; Yasmine Benhassine; Jean-François Paquin
Journal:  Org Biomol Chem       Date:  2015-02-28       Impact factor: 3.876

9.  Catalytic formation of C-O bonds by alkene activation: Lewis acid-cycloisomerisation of olefinic alcohols.

Authors:  Lydie Coulombel; Isabelle Favier; Elisabet Duñach
Journal:  Chem Commun (Camb)       Date:  2005-03-09       Impact factor: 6.222

Review 10.  Catalytic, Stereoselective Dihalogenation of Alkenes: Challenges and Opportunities.

Authors:  Alexander J Cresswell; Stanley T-C Eey; Scott E Denmark
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-02       Impact factor: 15.336
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