Synthesis of a diaryliodonium salt and its use in the direct arylation of andole: a two-step experiment for the organic teaching laboratory

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dc.contributor.author Prendergast, Aisling M.
dc.contributor.author Shanahan, Rachel
dc.contributor.author Hickey, Aobha
dc.contributor.author Harrington, Francis
dc.contributor.author Schönbauer, David
dc.contributor.author Byrne, Peter A.
dc.contributor.author Schnürch, Michael
dc.contributor.author McGlacken, Gerard P.
dc.date.accessioned 2020-08-05T12:46:24Z
dc.date.available 2020-08-05T12:46:24Z
dc.date.issued 2019-11-04
dc.identifier.citation Prendergast, A. M., Shanahan, R., Hickey, A., Harrington, F., Schönbauer, D., Byrne, P. A., Schnürch, M. and McGlacken, G. P. (2020) 'Synthesis of a Diaryliodonium Salt and Its Use in the Direct Arylation of Indole: A Two-Step Experiment for the Organic Teaching Laboratory', Journal of Chemical Education, 97(1), pp. 200-206. doi: 10.1021/acs.jchemed.9b00525 en
dc.identifier.volume 97 en
dc.identifier.startpage 200 en
dc.identifier.endpage 206 en
dc.identifier.issn 0021-9584
dc.identifier.uri http://hdl.handle.net/10468/10356
dc.identifier.doi 10.1021/acs.jchemed.9b00525 en
dc.description.abstract In the past decade, C–H functionalization has been a very active topic of research in both academia and industry. When a H atom is replaced by an aryl (or heteroaryl) group, the transformation is termed “direct arylation”. This approach to the formation of key (hetero)aryl–(hetero)aryl bonds is complementary to traditional methods, such as the Suzuki–Miyaura and Stille reactions. Direct arylation/C–H functionalization is not represented in the majority of undergraduate chemistry laboratory curricula. An experiment is described here in which students carry out a multistep process, synthesizing a diaryliodonium salt and using it in the direct arylation of indole. Important organic and organometallic chemistry concepts are covered, including catalysis, traditional cross-coupling, C–H functionalization, multistep reaction processes, and regioselectivity. The experiment was successfully carried out by third- and fourth-year students in two universities over a two-year period (four times in total). Both high-yielding and low-yielding chemical steps were encountered, and a number of pedagogical approaches evolved. en
dc.description.sponsorship European Cooperation in Science and Technology (European COST, Action CA15106 (C−H Activation in Organic Synthesis, CHAOS)) en
dc.format.mimetype application/pdf en
dc.language.iso en en
dc.publisher American Chemical Society en
dc.relation.uri https://pubs.acs.org/doi/abs/10.1021/acs.jchemed.9b00525
dc.rights © 2019 American Chemical Society and Division of Chemical Education, Inc. This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Chemical Education, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/abs/10.1021/acs.jchemed.9b00525 en
dc.subject Upper-division undergraduate en
dc.subject Organic chemistry en
dc.subject Laboratory instruction en
dc.subject Hands-on learning/manipulatives en
dc.subject Synthesis en
dc.subject Catalysis en
dc.title Synthesis of a diaryliodonium salt and its use in the direct arylation of andole: a two-step experiment for the organic teaching laboratory en
dc.type Article (peer-reviewed) en
dc.internal.authorcontactother Peter Byrne, Chemistry, University College Cork, Cork, Ireland. +353-21-490-3000 Email: peter.byrne@ucc.ie en
dc.internal.availability Full text available en
dc.check.info Access to this article is restricted until 12 months after publication by request of the publisher. en
dc.check.date 2020-11-04
dc.date.updated 2020-08-04T01:14:08Z
dc.description.version Accepted Version en
dc.internal.rssid 529445335
dc.contributor.funder Science Foundation Ireland en
dc.contributor.funder European Cooperation in Science and Technology en
dc.description.status Peer reviewed en
dc.identifier.journaltitle Journal Of Chemical Education en
dc.internal.copyrightchecked No
dc.internal.licenseacceptance Yes en
dc.internal.IRISemailaddress peter.byrne@ucc.ie en
dc.internal.IRISemailaddress g.mcglacken@ucc.ie en
dc.relation.project info:eu-repo/grantAgreement/SFI/SFI Investigator Programme/12/IP/1315/IE/The Direct Arylation of Pyrones, Coumarins, Pyridones and Quinolones/ en
dc.relation.project info:eu-repo/grantAgreement/SFI/SFI Research Centres/12/RC/2275/IE/Synthesis and Solid State Pharmaceutical Centre (SSPC)/ en


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