Literature DB >> 17288382

Synthesis of 3,4-disubstituted 2H-benzopyrans through C-C bond formation via electrophilic cyclization.

Shilpa A Worlikar1, Tanay Kesharwani, Tuanli Yao, Richard C Larock.   

Abstract

The electrophilic cyclization of substituted propargylic aryl ethers by I2, ICl, and PhSeBr produces 3,4-disubstituted 2H-benzopyrans in excellent yields. This methodology results in vinylic halides or selenides under mild reaction conditions and tolerates a variety of functional groups, including methoxy, alcohol, aldehyde, and nitro groups.

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Year:  2007        PMID： 17288382      PMCID： PMC2527782          DOI： 10.1021/jo062234s

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


  26 in total

1.  Synthesis of 2,3-disubstituted benzo[b]furans by the palladium-catalyzed coupling of o-iodoanisoles and terminal alkynes, followed by electrophilic cyclization.

Authors:  Dawei Yue; Tuanli Yao; Richard C Larock
Journal:  J Org Chem       Date:  2005-12-09       Impact factor: 4.354

2.  Circadian rhythm of anti-fungal prenylated chromene in leaves of Piper aduncum.

Authors:  Andreia de A Morandim; Débora Cristina B Bergamo; Massuo Jorge Kato; Alberto José Cavalheiro; Vanderlan da S Bolzani; Maysa Furlan
Journal:  Phytochem Anal       Date:  2005 Jul-Aug       Impact factor: 3.373

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.  Studies on acetylenic compounds. 32. Ring closure of propargyl ethers. 2.

Authors:  I Iwai; J Ide
Journal:  Chem Pharm Bull (Tokyo)       Date:  1963-08       Impact factor: 1.645

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.  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

8.  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

9.  A modular and concise total synthesis of (+/-)-daurichromenic acid and analogues.

Authors:  Hongjuan Hu; Tyler J Harrison; Peter D Wilson
Journal:  J Org Chem       Date:  2004-05-28       Impact factor: 4.354

10.  Pt(IV)-catalyzed cyclization of arene-alkyne substrates via intramolecular electrophilic hydroarylation.

Authors:  Stefan J Pastine; So Won Youn; Dalibor Sames
Journal:  Org Lett       Date:  2003-04-03       Impact factor: 6.005
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  11 in total

1.  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

2.  Simultaneous synthesis of both rings of chromenes via a benzannulation/o-quinone methide formation/electrocyclization cascade.

Authors:  Nilanjana Majumdar; Keith A Korthals; William D Wulff
Journal:  J Am Chem Soc       Date:  2011-12-16       Impact factor: 15.419

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.  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

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

8.  Photoinduced synthesis of new diisochromenochromen-4-ones and their antimicrobial activities.

Authors:  Mohamad Yusuf; Indu Solanki; Payal Jain
Journal:  ScientificWorldJournal       Date:  2012-05-01

9.  Gold(I)-catalyzed hydroarylation reaction of aryl (3-iodoprop-2-yn-1-yl) ethers: synthesis of 3-iodo-2H-chromene derivatives.

Authors:  Pablo Morán-Poladura; Eduardo Rubio; José M González
Journal:  Beilstein J Org Chem       Date:  2013-10-16       Impact factor: 2.883

Review 10.  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
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