A convenient method for the preparation of functionalized N-acylsulfenamides from primary amides

GRAPHICAL ABSTRACT

ABSTRACT

We have developed a convenient method for the synthesis of functionalized N-acylsulfenamides under mild conditions and in moderate to good yields. The designed method is based on the reaction of (5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)-disulfanyl derivatives with nitrogen nucleophiles generated from primary amides or imides and sodium hydride. The developed method allows for the preparation of N-acylsulfenamides bearing additional hydroxyl, carboxyl, or amino functionalities.

Keywords:

• Sulfenamide
• thiols
• amide
• phthalimide
• phosphorodithioic acid

Funding

The authors gratefully acknowledge the National Science Centre for financial support (grant no. 2013/09/B/ST5/01261).