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Preparation of Salicyl Alcohols and 9‐Arylxanthenes Using Sodium Salicylates and Bromo‐Hydrocarbons Mediated by PPh 3
Author(s) -
Zhang Jing,
Li LingJie,
Tang Yu,
Yang Jun,
Xu KaiTian,
Zhang YuanMing
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201701342
Subject(s) - chemistry , steric effects , alcohol , organic chemistry , sodium salicylate , sodium , reaction conditions , medicinal chemistry , catalysis
A highly efficient and convenient Barbier‐Grignard‐type reaction to give salicyl alcohols and novel facile protocol to furnish unsymmetrical 9‐arylxanthenes using sodium salicylates and unactivated bromo‐hydrocarbons are described. Of total 21 synthesized compounds, 18 compounds containing 14 alcohols and 4 9‐arylxanthenes are new compounds. The products were provided in yields among 38–99%. The electronic and steric effects of bromo‐hydrocarbons on the reaction were discussed. Based on experimental results, a plausible mechanism concerning direct formation of salicyl alcohol from salicylate and PhMgBr with the promotion of PPh 3 is proposed.