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CA Article / Feb 23, 2017

Monofluoroalkylation and alkylation of alcohols using non-volatile reagents

Authors:
  • Osvaldo Ascenso
  • Emilia Leitao
  • William Heggie
  • Rita Ventura
  • Christopher Maycock
Source:
Tetrahedron Journal, 23 February 2017

Non-volatile S-Alkyl-S-phenyl-2,3,4,5-tetramethylphenylsulfonium triflate or tetrafluoroborate salts have been used to alkylate alcohols in the presence of sodium hydride. This is a simple and efficient method for the synthesis of ethers from complex alcohols and an alternative to the usual O-alkylation methods. This method was especially important for the preparation of monofluoromethyl ethers of a wide range of alcohols. Some alkylated derivatives of the precursors of some bioactive compounds were also prepared using these reagents.

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