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Tandem Arylation/Friedel‐Crafts Reaction of O ‐Hydroxy Bisbenzylic Alcohols with Diaryliodonium Salts: One Pot Synthesis of Unsymmetrical 9‐Arylxanthenes
Author(s) -
Mao Song,
Hua Zerui,
Wu Xunshen,
Yang Yang,
Han Jianwei,
Wang Limin
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201600036
Subject(s) - tandem , yield (engineering) , friedel–crafts reaction , chemistry , brønsted–lowry acid–base theory , base (topology) , catalysis , organic chemistry , reaction conditions , combinatorial chemistry , materials science , mathematics , mathematical analysis , metallurgy , composite material
A one‐pot synthesis of 9‐arylxanthenes from easily prepared o ‐hydroxy bisbenzylic alcohols and diaryliodonium salts has been reported. O ‐hydroxy bisbenzylic alcohols were utilized to generate carbinols in situ with diaryliodonium salts promoted by base. Carbinols were then subjected to Brønsted acid catalyzed cyclization to furnish 9‐arylxanthenes. A variety of symmetrical and unsymmetrical 9‐aryxanthenes have been prepared assisted by base and Brønsted acid under mild conditions with satisfactory yields (up to 95 % yield). Furthermore, the procedure is capable of tolerating a wide range of substrates (36 examples).