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Synthesis of Phenols and Aryl Silyl Ethers via Arylation of Complementary Hydroxide Surrogates
Author(s) -
Marcus Reitti,
Ramani Gurubrahamam,
Melanie Walther,
Erik Lindstedt,
Berit Olofsson
Publication year - 2018
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.8b00287
Subject(s) - chemistry , phenols , silylation , nucleophile , aryne , aryl , hydroxide , organic chemistry , reactivity (psychology) , hydrogen peroxide , combinatorial chemistry , catalysis , medicine , alkyl , alternative medicine , pathology
Two transition-metal-free methods to access substituted phenols via the arylation of silanols or hydrogen peroxide with diaryliodonium salts are presented. The complementary reactivity of the two nucleophiles allows synthesis of a broad range of phenols without competing aryne formation, as illustrated by the synthesis of the anesthetic Propofol. Furthermore, silyl-protected phenols can easily be obtained, which are suitable for further transformations.

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