期刊
JOURNAL OF CHEMICAL EDUCATION
卷 97, 期 1, 页码 200-206出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.jchemed.9b00525
关键词
Upper-Division Undergraduate; Organic Chemistry; Laboratory Instruction; Hands-On Learning/Manipulatives; Synthesis; Catalysis
资金
- Science Foundation Ireland (SFI)
- Synthesis and Solid State Pharmaceutical Centre (SSPC) [SFI/12/IP/1315, SFI/12/RC/2275]
- European COST, Action [CA15106]
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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