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
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.