Rapid modular synthesis of indole ethers via dehydrogenative cross-coupling reaction of indoles and alcohols

Literature Information

Publication Date 2023-11-14
DOI 10.1039/D3QO01501G
Impact Factor 5.281
Authors

Mao-Gui Huang, Xiao-Hong Chen, Hai-Bing Xu, Yue-Jin Liu


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Abstract

Indole ethers are commonly found in pharmaceuticals, enzymes, and many bioactive compounds. The cross-coupling of indoles and alcohols by activation of the indole C–H bond would provide a direct and economical way of making these medicinally active products, but this remains an elusive transformation. Here we describe a straightforward and economical protocol for the synthesis of indole ethers by indole C–H alkoxylation with cobalt catalysis. A variety of functionalized indole ethers were modularly prepared from readily accessible indoles and alcohols. The scope of the transformation was expanded to a challenging intermolecular type reaction for the one-step construction of the core scaffold of piboserod (a 5-HT4 receptor antagonist). The synthetic applications were further demonstrated by the diversification of products and synthesis of many medical agent analogues. Preliminary mechanistic investigations indicated that the salicylaldehyde-cobalt catalyst played a key role in promoting this transformation.

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Contents list

2023-12-14 Front/Back Matter

DOI: 10.1039/D3CC90406G

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Source Journal

Organic Chemistry Frontiers

Organic Chemistry Frontiers
CiteScore: 7.8
Self-citation Rate: 8.7%
Articles per Year: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

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