A Simple and Mild Synthesis of 1H-Isochromenes and (Z)-1-Alkylidene-1,3-dihydroisobenzofurans by the Iodocyclization of 2-(1-Alkynyl)benzylic Alcohols

dc.contributor.author Mancuso, Raffaella
dc.contributor.author Mehta, Saurabh
dc.contributor.author Jenks, William
dc.contributor.author Gabriele, Bartolo
dc.contributor.author Salerno, Giuseppe
dc.contributor.author Jenks, William
dc.contributor.author Larock, Richard
dc.contributor.department Chemistry
dc.date 2018-02-17T06:54:06.000
dc.date.accessioned 2020-06-30T01:18:25Z
dc.date.available 2020-06-30T01:18:25Z
dc.date.copyright Fri Jan 01 00:00:00 UTC 2010
dc.date.issued 2009-12-31
dc.description.abstract <p>A variety of iodo-substituted isochromenes, dihydroisobenzofurans, and pyranopyridines are readily prepared in good to excellent yields under mild conditions by the iodocyclization of readily available 2-(1-alkynyl)benzylic alcohols or 2-(1-alkynyl)-3-(hydroxymethyl)pyridines. Reactions are carried out in MeCN at 25 °C with 3 equiv of I2 as the iodine source and NaHCO3 (3 equiv) as the base. The regiochemical outcome of the reaction strongly depends on the substitution pattern of the starting material. In particular, the 5-<em>exo</em>-<em>dig</em> cyclization mode, leading to dihydroisobenzofurans, is observed in the case of substrates bearing a tertiary alcoholic group, owing to the <em>gem</em>-dialkyl effect, while the 6-<em>endo</em>-<em>dig</em> cyclization mode, leading to isochromene or pyranopyridines, is the usually preferred pathway in the case of substrates bearing a primary or secondary alcoholic group.</p>
dc.description.comments <p>Reprinted (adapted) with permission from <em>The Journal of Organic Chemistry</em>, 75(3); 897-901. Doi: <a href="http://dx.doi.org/10.1021/jo902333y" target="_blank">10.1021/jo902333y</a>. Copyright 2009 American Chemical Society.</p>
dc.format.mimetype application/pdf
dc.identifier archive/lib.dr.iastate.edu/chem_pubs/208/
dc.identifier.articleid 1201
dc.identifier.contextkey 7889087
dc.identifier.s3bucket isulib-bepress-aws-west
dc.identifier.submissionpath chem_pubs/208
dc.identifier.uri https://dr.lib.iastate.edu/handle/20.500.12876/14649
dc.language.iso en
dc.source.bitstream archive/lib.dr.iastate.edu/chem_pubs/208/0-2010_JenksWS_ACS_License_SimpleMildSynthesis.pdf|||Fri Jan 14 22:28:37 UTC 2022
dc.source.bitstream archive/lib.dr.iastate.edu/chem_pubs/208/2010_JenksWS_SimpleMildSynthesis.pdf|||Fri Jan 14 22:28:38 UTC 2022
dc.source.uri 10.1021/jo902333y
dc.subject.disciplines Chemistry
dc.subject.disciplines Materials Chemistry
dc.subject.disciplines Organic Chemistry
dc.subject.disciplines Other Chemistry
dc.subject.disciplines Polymer Chemistry
dc.title A Simple and Mild Synthesis of 1H-Isochromenes and (Z)-1-Alkylidene-1,3-dihydroisobenzofurans by the Iodocyclization of 2-(1-Alkynyl)benzylic Alcohols
dc.type article
dc.type.genre article
dspace.entity.type Publication
relation.isAuthorOfPublication 4bd6268b-7134-4d6d-9050-46681c12c965
relation.isOrgUnitOfPublication 42864f6e-7a3d-4be3-8b5a-0ae3c3830a11
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