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Direct Oxidative Arylation of C( sp 3 )H Bonds Adjacent to Oxygen of Ethers and Alcohols
Author(s) -
Pandit Rameshwar Prasad,
Lee Yong Rok
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400295
Subject(s) - chemistry , moiety , phenol , trifluoromethanesulfonate , oxygen , palladium , medicinal chemistry , oxidative coupling of methane , quinone , organic chemistry , catalysis
The direct arylation of C( sp 3 )H bonds adjacent to oxygen in ethers with phenol and naphthol derivatives was developed via palladium(II) acetate/copper(II) triflate [Pd(OAc) 2 /Cu(OTf) 2 ]‐catalyzed cross‐dehydrgenative coupling in the presence of tert ‐butyl hyroperoxide (TBHP). This process provides exclusive installation of a tetrahydrofuranyl moiety at a more hindered position of multiply substituted phenol derivatives. The cross‐dehydrogenative coupling of 1,4‐dihydroxynaphthalene with cyclic ethers and free alcohols afforded biologically interesting 2‐substituted 1,4‐naphthoquinone derivatives.