Assembly of Indolo[2,1-a]isoquinolines via a C-H Oxidation/Carbene Insertion Cascade
Qiyuan Ma1, Yuhao Zhu2, Jincheng Wang1
1School of Chemistry & Materials, Yangzhou University, Yangzhou, Jiangsu 225002, China.
Abstract:
A metal-free synthesis of indolo[2,1-a]isoquinolines is achieved via a one-pot C-H oxidation/intramolecular carbene insertion cascade. The strategy employs CBr4 as a mild oxidant and diazoacetates to form key α-diazo intermediates, which undergo visible-light-induced denitrogenative cyclization to forge the target framework. This protocol features operational simplicity, excellent functional group tolerance, and scalability, enabling the discovery of derivatives with aggregation-induced emission properties.
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Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
