Recent advances in electrochemically enabled construction of indoles from non-indole-based substrates

• Published in: Chemical communications (Cambridge, England) England), 2024-08, Vol.6 (65), p.8516-8525
• Main Authors: Zheng, Yu, Chen, Chunxi, Lu, Yanju, Huang, Shenlin
• Format: Article
• Language: English
• Subjects: Agrochemicals; Chemical synthesis; Electrochemistry; Indoles; Natural products; Oxidizing agents; Regioselectivity; Substrates
• ISSN: 1359-7345; 1364-548X; 1364-548X
• DOI: 10.1039/d4cc03040k

Indole motifs are important heterocycles found in natural products, pharmaceuticals, agricultural chemicals, and materials. Although there are well-established classical name reactions for indole synthesis, these transformations often require harsh reaction conditions, have a limited substrate scope, and exhibit poor regioselectivity. As a result, organic synthesis chemists have been exploring efficient and practical methods, leading to numerous strategies for synthesizing a variety of functionalized indoles. In recent years, electrochemistry has emerged as an environmentally friendly and sustainable synthetic tool, with widespread applications in organic synthesis. This technology allows for elegant synthetic routes to be developed for the construction of indoles under external oxidant-free conditions. This feature article specifically focuses on recent advancements in indole synthesis from non-indole-based substrates, as well as the mechanisms underlying these transformations. This review summarizes recent advances in the electrochemically enabled construction of indoles from non-indole-based precursors and their underlying mechanisms.