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Aryl[2‐(hydroxypro‐2‐yl)cyclohyxyl]dimethylsilane: A Robust Aryl(trialkyl)silane Reagent for Nickel‐catalyzed Cross‐coupling Reactions with Aryl Tosylates
Author(s) -
Tang Shi,
Li ShuHua,
Nakao Yoshiaki,
Hiyama Tamejiro
Publication year - 2013
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201300031
Subject(s) - aryl , dimethylsilane , chemistry , reagent , silane , catalysis , nickel , ether , organic chemistry , coupling reaction , alkyl
A general route for the synthesis of an aryl(trialkyl)silane reagent, aryl[2‐(hydroxypro‐2‐yl)cyclohexyl]dimethylsilane, is demonstrated. By using a carbonate salt as an activator, the robust aryl(trialkyl)silane promotes nickel‐catalyzed aryl–aryl cross‐coupling reactions with aryl tosylates in a fluoride‐free and highly chemoselective manner. A reusable cyclic silyl ether was also quantitatively recovered.