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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Prendergast, Aisling M.
Shanahan, Rachel
Hickey, Aobha
Harrington, Francis
Schönbauer, David
Byrne, Peter A.
Schnürch, Michael
McGlacken, Gerard P.
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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.
Upper-division undergraduate , Organic chemistry , Laboratory instruction , Hands-on learning/manipulatives , Synthesis , Catalysis
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
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