Literature DB >> 16526778

Synthesis of 2,3-disubstituted benzo[b]selenophenes via electrophilic cyclization.

Tanay Kesharwani1, Shilpa A Worlikar, Richard C Larock.   

Abstract

2,3-Disubstituted benzo[b]selenophenes have been prepared by the electrophilic cyclization of various 1-(1-alkynyl)-2-(methylseleno)arenes by Br2, NBS, I2, ICl, PhSeCl, PhSeBr, and Hg(OAc)2. This method tolerates a wide variety of functional groups, including alcohol, ester, nitrile, nitro, and silyl groups, and proceeds under exceptionally mild reaction conditions.

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Year:  2006        PMID： 16526778      PMCID： PMC2527062          DOI： 10.1021/jo0524268

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


  16 in total

1.  IPy2BF4-promoted intramolecular addition of masked and unmasked anilines to alkynes: direct assembly of 3-iodoindole cores.

Authors:  José Barluenga; Mónica Trincado; Eduardo Rubio; José M González
Journal:  Angew Chem Int Ed Engl       Date:  2003-05-30       Impact factor: 15.336

2.  2,6-Diphenylbenzo[1,2-b:4,5-b']dichalcogenophenes: a new class of high-performance semiconductors for organic field-effect transistors.

Authors:  Kazuo Takimiya; Yoshihito Kunugi; Yasushi Konda; Naoto Niihara; Tetsuo Otsubo
Journal:  J Am Chem Soc       Date:  2004-04-28       Impact factor: 15.419

3.  Synthesis of substituted isoquinolines by electrophilic cyclization of iminoalkynes.

Authors:  Qinhua Huang; Jack A Hunter; Richard C Larock
Journal:  J Org Chem       Date:  2002-05-17       Impact factor: 4.354

4.  The synthesis and tubulin binding activity of thiophene-based analogues of combretastatin A-4.

Authors:  B L Flynn; G P Flynn; E Hamel; M K Jung
Journal:  Bioorg Med Chem Lett       Date:  2001-09-03       Impact factor: 2.823

5.  Synthesis of 2,3-disubstituted benzo[b]thiophenes via palladium-catalyzed coupling and electrophilic cyclization of terminal acetylenes.

Authors:  Dawei Yue; Richard C Larock
Journal:  J Org Chem       Date:  2002-03-22       Impact factor: 4.354

6.  Synthesis of isocoumarins and alpha-pyrones via electrophilic cyclization.

Authors:  Tuanli Yao; Richard C Larock
Journal:  J Org Chem       Date:  2003-07-25       Impact factor: 4.354

7.  Photobiological activity of sulphur and selenium analogues of psoralen.

Authors:  A Jakobs; J Piette
Journal:  J Photochem Photobiol B       Date:  1994-01       Impact factor: 6.252

8.  Synthesis of polycyclic aromatic iodides via ICl-induced intramolecular cyclization.

Authors:  Tuanli Yao; Marino A Campo; Richard C Larock
Journal:  Org Lett       Date:  2004-08-05       Impact factor: 6.005

9.  Synthesis of 3-iodoindoles by electrophilic cyclization of N,N-dialkyl-2-(1-alkynyl)anilines.

Authors:  Dawei Yue; Richard C Larock
Journal:  Org Lett       Date:  2004-03-18       Impact factor: 6.005

10.  Efficient syntheses of heterocycles and carbocycles by electrophilic cyclization of acetylenic aldehydes and ketones.

Authors:  Dawei Yue; Nicola Della Cà; Richard C Larock
Journal:  Org Lett       Date:  2004-05-13       Impact factor: 6.005
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  10 in total

1.  Green Synthesis of Halogenated Thiophenes, Selenophenes and Benzo[b]selenophenes Using Sodium Halides as a Source of Electrophilic Halogens.

Authors:  Tanay Kesharwani; Krystal A Giraudy; Jordan L Morgan; Cory Kornman; Abayomi D Olaitan
Journal:  Tetrahedron Lett       Date:  2017-01-07       Impact factor: 2.415

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

Review 3.  Recent Advances in the Synthesis of Selenophenes and Their Derivatives.

Authors:  Paola S Hellwig; Thiago J Peglow; Filipe Penteado; Luana Bagnoli; Gelson Perin; Eder J Lenardão
Journal:  Molecules       Date:  2020-12-13       Impact factor: 4.411

4.  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

5.  A novel synthetic route to 3-sulfenyl- and 3-selenylindoles by n-Bu4NI-induced electrophilic cyclization.

Authors:  Yu Chen; Chul-Hee Cho; Richard C Larock
Journal:  Org Lett       Date:  2009-01-01       Impact factor: 6.005

6.  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

7.  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

8.  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

9.  A one-pot successive cyclization-alkylation strategy for the synthesis of 2,3-disubstituted benzo[b]thiophenes.

Authors:  Christopher Cunningham; Matthew Cloyd; Aimee Phillips; Soha Khan; Katherine Whalen; Tanay Kesharwani
Journal:  Org Biomol Chem       Date:  2021-05-12       Impact factor: 3.876

10.  Iodocyclization in Aqueous Media and Supramolecular Reaction Control Using Water-Soluble Hosts.

Authors:  Treyvon Bokoskie; Christopher Cunningham; Cory Kornman; Tanay Kesharwani; Mahesh Pattabiraman
Journal:  ACS Omega       Date:  2019-10-17
  10 in total

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