4.8 Article

4,5-Dimethyl-2-Iodoxybenzenesulfonic Acid Catalyzed Site-Selective Oxidation of 2-Substituted Phenols to 1,2-Quinols

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 14, Pages 3956-3960

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201612463

Keywords

hypervalent compounds; iodine; oxidation; phenol; silicon

Funding

  1. JSPS.KAKENHI [15H05755, 15H05484, 24245020]
  2. Program for Leading Graduate Schools: IGER Program in Green Natural Sciences (MEXT)
  3. JSPS Research Fellowship for Young Scientists
  4. Grants-in-Aid for Scientific Research [15H05484, 14J10428] Funding Source: KAKEN

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A site-selective hydroxylative dearomatization of 2-substituted phenols to either 1,2-benzoquinols or their cyclodimers, catalyzed by 4,5-dimethyl-2-iodoxybenzenesulfonic acid with Oxone, has been developed. Natural products such as biscarvacrol and lacinileneC methyl ether could be synthesized efficiently under mild reaction conditions. Furthermore, both the reaction rate and site selectivity could be further improved by the introduction of a trialkylsilylmethyl substituent at the 2-position of phenols. The corresponding 1,2-quinols could be transformed into various useful structural motifs by [4+2] cycloaddition cascade reactions.

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