Methyltrichlorosilane as an Effective Activation Agent for Swern Oxidation

Abstract

A practical and efficient alternative version of the Swern oxidation has been successfully developed. Methyltrichlorosilane was used as an efficient activator of dimethylsulfoxide, which could oxidize a wide range of primary and secondary alcohols to the corresponding carbonyl compounds with good to excellent yields.

GRAPHICAL ABSTRACT

Keywords:

• Alcohols
• carbonyl compounds
• MeSiCl₃–DMSO
• silicon reagents
• Swern oxidation

Notes

^a Conditions: [1] = 0.3 M, [chlorosilane] = 0.3 M, [DMSO] = 1.2 M, [Et₃N] = 2.4 M.

^b All chlorosilanes were used directly without purification.

^c The yield was determined with HPLC.

^a Conditions: [Alcohol] = 0.5 M, [MeSiCl₃] = 0.5 M, [DMSO] = 2 M.

^b The yield was determined with ¹H NMR.

^c Reaction was carried out at −20 °C.

^a,b,c See Refs. [3b], [3h], and [4c] for all the reaction conditions. TCT = 2,4,6-trichloro-1,3,5-triazine.

^d Conditions: [alcohol] = 0.5 M, [MeSiCl₃] = 0.5 M, [DMSO] = 2 M.

^e The yield was determined with ¹H NMR.