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.contributor.funder	Science Foundation Ireland	en
dc.contributor.funder	European Cooperation in Science and Technology	en
dc.date.accessioned	2020-08-05T12:46:24Z
dc.date.available	2020-08-05T12:46:24Z
dc.date.issued	2019-11-04
dc.date.updated	2020-08-04T01:14:08Z
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.description.status	Peer reviewed	en
dc.description.version	Accepted Version	en
dc.format.mimetype	application/pdf	en
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.doi	10.1021/acs.jchemed.9b00525	en
dc.identifier.endpage	206	en
dc.identifier.issn	0021-9584
dc.identifier.journaltitle	Journal Of Chemical Education	en
dc.identifier.startpage	200	en
dc.identifier.uri	https://hdl.handle.net/10468/10356
dc.identifier.volume	97	en
dc.language.iso	en	en
dc.publisher	American Chemical Society	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
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

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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