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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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Date
2019-11-04
Authors
Prendergast, Aisling M.
Shanahan, Rachel
Hickey, Aobha
Harrington, Francis
Schönbauer, David
Byrne, Peter A.
Schnürch, Michael
McGlacken, Gerard P.
Journal Title
Journal ISSN
Volume Title
Publisher
American Chemical Society
Published Version
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.
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Keywords
Upper-division undergraduate , Organic chemistry , Laboratory instruction , Hands-on learning/manipulatives , Synthesis , Catalysis
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
Copyright
© 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