Journal
TETRAHEDRON
Volume 127, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2022.133101
Keywords
Oxidative rearrangement of indoles; Halide catalysis; Hydrogen peroxide; Metal -free oxidation
Categories
Funding
- Science and Tech-nology Plan Project of Taizhou
- [22gyb10]
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This paper presents an efficient metal-free method for the oxidative rearrangement of indoles, leading to the formation of various organic compounds. The protocol exhibits a broad substrate scope and functional group tolerance, and has been successfully applied in natural product synthesis.
Oxidative rearrangement of indoles is an essential transformation that has been widely used in the synthesis of many pharmaceutical agents and bioactive natural products. Herein, we report an efficient, practical and metal-free method for the oxidative rearrangement of indoles to spirooxindoles, 2-oxindoles, 2,2-disubstituted indolin-3-ones, and oxa-spirooxindoles using 10 mol% HBr and hydrogen peroxide as the terminal oxidant. The protocol displays a broad substrate scope (35 examples) and a wide range of functional group tolerance and has been applied in the synthesis of (+/-)-coerulescine and the formal synthesis of (+/-)-horsfiline. Notably, the distinct advantages of this protocol involve metal-free catalysis, waste prevention, and simple operation.(c) 2022 Elsevier Ltd. All rights reserved.
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