N-Trifluoromethylthiolated Sulfoximines

Area of Science:

• Organic Chemistry
• Sulfur Chemistry
• Fluorine Chemistry

Background:

• Sulfoximines are versatile functional groups in organic synthesis.
• N-functionalized sulfoximines are important building blocks.
• Stable trifluoromethylthio (SCF3) compounds are highly sought after.

Purpose of the Study:

• To develop a reliable method for synthesizing air- and moisture-stable N-trifluoromethylthio sulfoximines.
• To provide access to previously difficult-to-prepare sulfoximine derivatives.

Main Methods:

• A two-step synthesis starting from N-H-sulfoximines.
• Step 1: Bromination of the sulfoximine nitrogen.
• Step 2: Reaction of the N-bromo intermediate with silver trifluoromethanethiolate.

Main Results:

• Excellent yields of N-trifluoromethylthio sulfoximines were achieved.
• The products exhibit air- and moisture stability.
• A one-pot reaction sequence was also demonstrated for specific cases.

Conclusions:

• A robust and efficient synthetic route to N-trifluoromethylthio sulfoximines has been established.
• This method broadens the accessibility of functionalized sulfoximines.
• The developed protocol is suitable for both standard and one-pot procedures.