Literature DB >> 17555360

Synthesis of 4-iodo-3-furanones utilizing electrophile-induced tandem cyclization/1,2-migration reactions.

Benedikt Crone1, Stefan F Kirsch.   

Abstract

Two protocols for the construction of 4-iodo-3-furanones through a sequence consisting of cyclization and 1,2-migration of 2-alkynyl-2-silyloxy carbonyl compounds were developed. In one, electrophilic cyclization is directly induced by N-iodosuccinimide (NIS). In the second less limited variant, AuCl3 catalyzes the tandem reaction in the presence of NIS to provide highly substituted heterocycles in moderate to excellent yields.

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Year:  2007        PMID： 17555360     DOI： 10.1021/jo070695n

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  9 in total

1.  Intramolecular Diamination and Alkoxyamination of Alkenes with N-Sulfonyl Ureas With N-Iodosuccinimide.

Authors:  Hao Li; Ross A Widenhoefer
Journal:  Tetrahedron       Date:  2010-06-26       Impact factor: 2.457

2.  Synthesis of 3-sulfenyl- and 3-selenylindoles by the Pd/Cu-catalyzed coupling of N,N-dialkyl-2-iodoanilines and terminal alkynes, followed by n-Bu(4)NI-induced electrophilic cyclization.

Authors:  Yu Chen; Chul-Hee Cho; Feng Shi; Richard C Larock
Journal:  J Org Chem       Date:  2009-09-04       Impact factor: 4.354

3.  Iodine/palladium approaches to the synthesis of polyheterocyclic compounds.

Authors:  Saurabh Mehta; Richard C Larock
Journal:  J Org Chem       Date:  2010-03-05       Impact factor: 4.354

4.  Competition studies in alkyne electrophilic cyclization reactions.

Authors:  Saurabh Mehta; Jesse P Waldo; Richard C Larock
Journal:  J Org Chem       Date:  2009-02-06       Impact factor: 4.354

5.  Metal-catalyzed 1,2-shift of diverse migrating groups in allenyl systems as a new paradigm toward densely functionalized heterocycles.

Authors:  Alexander S Dudnik; Anna W Sromek; Marina Rubina; Joseph T Kim; Alexander V Kel'in; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2008-01-04       Impact factor: 15.419

6.  A simple and mild synthesis of 1H-isochromenes and (Z)-1-alkylidene-1,3-dihydroisobenzofurans by the iodocyclization of 2-(1-alkynyl)benzylic alcohols.

Authors:  Raffaella Mancuso; Saurabh Mehta; Bartolo Gabriele; Giuseppe Salerno; William S Jenks; Richard C Larock
Journal:  J Org Chem       Date:  2010-02-05       Impact factor: 4.354

7.  When gold can do what iodine cannot do: A critical comparison.

Authors:  Sara Hummel; Stefan F Kirsch
Journal:  Beilstein J Org Chem       Date:  2011-06-22       Impact factor: 2.883

Review 8.  Light-Induced Mechanistic Divergence in Gold(I) Catalysis: Revisiting the Reactivity of Diazonium Salts.

Authors:  Svenja Taschinski; René Döpp; Martin Ackermann; Frank Rominger; Folkert de Vries; Maximilian F S J Menger; Matthias Rudolph; A Stephen K Hashmi; Johannes E M N Klein
Journal:  Angew Chem Int Ed Engl       Date:  2019-10-11       Impact factor: 15.336

9.  A tandem Mannich addition-palladium catalyzed ring-closing route toward 4-substituted-3(2H)-furanones.

Authors:  Jubi John; Eliza Târcoveanu; Peter G Jones; Henning Hopf
Journal:  Beilstein J Org Chem       Date:  2014-06-27       Impact factor: 2.883
  9 in total

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