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?-Acetoxyarone synthesis via iodine-catalyzed and tert-butyl hydroperoxide-mediateded self-intermolecular oxidative coupling of aryl ketones.

ABSTRACT: We present a metal-free method for ?-acetoxyarone synthesis by self-intermolecular oxidative coupling of aryl ketones using I₂-tert-butyl hydroperoxide (TBHP). Under the optimum conditions, various aryl ketones gave the corresponding products in moderate to excellent yields. A series of control experiments were performed; the results suggest the involvement of radical pathways. Multiple radical intermediates were generated in situ and the overall process involved several different reactions, which proceeded self-sequentially in a single reactor. A labeling experiment using ¹⁸O-labeled H₂O confirmed that the oxygen in the product was derived from TBHP, not from H₂O in the TBHP solvent.

SUBMITTER: Tan L

PROVIDER: S-EPMC5480364 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

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α-Acetoxyarone synthesis via iodine-catalyzed and tert-butyl hydroperoxide-mediateded self-intermolecular oxidative coupling of aryl ketones.

Tan Liquan L Chen Cui C Liu Weibing W

Beilstein journal of organic chemistry 20170606

We present a metal-free method for α-acetoxyarone synthesis by self-intermolecular oxidative coupling of aryl ketones using I2-tert-butyl hydroperoxide (TBHP). Under the optimum conditions, various aryl ketones gave the corresponding products in moderate to excellent yields. A series of control experiments were performed; the results suggest the involvement of radical pathways. Multiple radical intermediates were generated in situ and the overall process involved several differ ...[more]

PMID: 28684987

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