Ph3P/CCl4 as a highly efficient reagent for one-pot N-alkylation of sulfonamides from alcohols: a rapid route to N-alkyl sulfonamides synthesis.
A mild, efficient, and selective protocol for the one-pot N-alkylation of sulfonamides with alcohols using triphenylphosphine and carbon tetrachloride is described. In this method, treatment of alcohols with a mixture of triphenylphosphine, carbon tetrachloride, and potassium sulfonylamide salts in refluxing anhydrous DMF furnishes the corresponding N-alkyl sulfonamides in good to excellent yields. This protocol is highly efficient for various structurally diverse alcohols and potassium sulfonylamide salts. In this paper the influence of solvents and various reagents as sources for electrophilic-halogen instead of carbon tetrachloride in combination with triphenylphosphine have been examined. This protocol demonstrates the selectivity between primary and secondary alcohols. A plausible mechanism for this protocol has been described.
Department of Chemistry, Shiraz University of Technology, Shiraz, 71555-313, Iran, soltani@sutech.ac.ir.
Mohammad Navid Soltani
MN
Rad
Somayeh
S
Behrouz
D000438:Alcohols / Q000737:chemistry*; D000478:Alkylation; D002251:Carbon Tetrachloride / Q000737:chemistry*; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry
D000438:Alcohols; D009943:Organophosphorus Compounds; D012997:Solvents; D013449:Sulfonamides; C061896:triphenylphosphine; D002251:Carbon Tetrachloride