Synthesis of a Diaryliodonium Salt and Its Use in the Direct Arylation of Indole: A Two-Step Experiment for the Organic Teaching Laboratory

• Aisling M. Prendergast ^[1] ; Rachel Shanahan ^[1] ; Aobha Hickey ^[1] ; Francis Harrington ^[1] ; David Schönbauer ^[2] ; Peter A. Byrne ^[1] ; Michael Schnürch ^[2] ; Gerard P. McGlacken ^[1]
  1. [1] University College Cork

     University College Cork

     Irlanda

     
  2. [2] Vienna University of Technology

     Vienna University of Technology

     Innere Stadt, Austria

     
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 97, Nº 1, 2020, págs. 200-206
• Idioma: inglés
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• Resumen

  • 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.