Gold(i)-catalysed dehydrative formation of ethers from benzylic alcohols and phenols

Abstract

A well-defined NHC–gold(i) complex has been shown highly effective in the formation of ethers from secondary benzylic alcohols and phenols under mild reaction conditions.

Zirconium-catalysed direct substitution of alcohols: enhancing the selectivity by kinetic analysis

“…Phenols have been reported to serve as both O-and C-nucleophiles in Lewis acid catalysed direct substitution of alcohols. 52,106 With our conditions, phenolic -OH groups were unreactive as O-nucleophiles, which allowed for mono-etherification of diols with full selectivity for the aliphatic alcohol (Scheme 2C). Due to low solubility of the diols in BTF, these reactions were carried out in THF.…”

Inner-Sphere versus Outer-Sphere Coordination of BF4– in a NHC-Gold(I) Complex

“…On the basis of our experience with NHC-monogold , and (hydroxide bridged) NHC-digold complexes containing BF 4 counterions, the synthesis of [Au­(NHC)­(FBF 3 )]/[Au­(NHC)­(L)]­[BF 4 ]/ (type II / VI ) was targeted. The synthesis was first approached by performing metathesis reactions of [Au­(NHC)­(Cl)] with AgBF 4 in CH 2 Cl 2 , a poorly coordinating solvent.…”

N-Halosuccinimides as Precatalysts for C-, N-, O-, and X-Nucleophilic Substitution Reactions of Alcohols under Mild Reaction Conditions

“…Many related transformations, including the use of Brønsted and Lewis acids, metal ions, or other supporters in a substoichiometric amount, have been reported by several reviews [3][4][5][6][7][8][9][10][11][12][13] and recent related advanced reports [14][15][16][17][18]. However, the requirement of toxic or expensive reagents, environmentally undesirable solvents, a high concentration of the mediator, prolonged reaction time, or high temperature make such a method less attractive from the green chemical aspect.…”