Literature DB >> 15369355

Cyclization of carbonyl groups onto alkynes upon reaction with IPy2BF4 and their trapping with nucleophiles: a versatile trigger for assembling oxygen heterocycles.

José Barluenga1, Henar Vázquez-Villa, Alfredo Ballesteros, José M González.   

Abstract

Iodonium ions liberated from bis(pyridine)iodonium(I) tetrafluoroborate react with ortho-alkynyl-substituted carbonyl compounds and different nucleophiles to give valuable iodinated heterocycles at room temperature, through a new and metal-free reaction sequence. Interestingly, the nature of the nucleophile can be widely modified, and not only alcohols but also several carbon-based nucleophiles can be nicely used.

Entities:  

Year:  2003        PMID: 15369355     DOI: 10.1021/ja0355372

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  16 in total

1.  Syntheses of isochromenes and naphthalenes by electrophilic cyclization of acetylenic arenecarboxaldehydes.

Authors:  Dawei Yue; Nicola Della Ca; Richard C Larock
Journal:  J Org Chem       Date:  2006-04-28       Impact factor: 4.354

2.  Stereoselective synthesis of tertiary ethers through geometric control of highly substituted oxocarbenium ions.

Authors:  Lei Liu; Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2010-08-09       Impact factor: 15.336

3.  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

4.  Synthesis of 3-iodoindoles by the Pd/Cu-catalyzed coupling of N,N-dialkyl-2-iodoanilines and terminal acetylenes, followed by electrophilic cyclization.

Authors:  Dawei Yue; Tuanli Yao; Richard C Larock
Journal:  J Org Chem       Date:  2006-01-06       Impact factor: 4.354

5.  Synthesis of naphthalenes and 2-naphthols by the electrophilic cyclization of alkynes.

Authors:  Xiaoxia Zhang; Sampa Sarkar; Richard C Larock
Journal:  J Org Chem       Date:  2006-01-06       Impact factor: 4.354

6.  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

7.  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

8.  The synthesis of highly substituted isoxazoles by electrophilic cyclization: an efficient synthesis of valdecoxib.

Authors:  Jesse P Waldo; Richard C Larock
Journal:  J Org Chem       Date:  2007-11-03       Impact factor: 4.354

9.  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

10.  Synthesis of Substituted Quinolines by the Electrophilic Cyclization of N-(2-Alkynyl)anilines.

Authors:  Xiaoxia Zhang; Tuanli Yao; Marino A Campo; Richard C Larock
Journal:  Tetrahedron       Date:  2010-02-06       Impact factor: 2.457

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