Mild Reductive Functionalization of Amides into N-Sulfonylformamidines
Paz Trillo1, Tove Slagbrand1, Fredrik Tinnis1
1Department of Organic Chemistry Stockholm University 106 91 Stockholm Sweden.
Chemistryopen
|August 11, 2017
Summary
A new one-pot protocol efficiently converts tertiary amides into N-sulfonylformamidines. This method utilizes mild catalytic reduction to enamines followed by reaction with sulfonyl azides, offering a valuable synthetic route.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Catalysis
Background:
- Amide functionalization is crucial in organic synthesis.
- Developing efficient methods for N-sulfonylformamidine synthesis is of interest.
- Existing methods may require harsh conditions or multiple steps.
Purpose of the Study:
- To report a novel one-pot protocol for the reductive functionalization of amides.
- To synthesize N-sulfonylformamidines from tertiary amides.
- To establish a mild and efficient catalytic reduction method.
Main Methods:
- Utilized molybdenum hexacarbonyl (Mo(CO)6) and 1,1,3,3-tetramethyldisiloxane (TMDS) for mild catalytic reduction.
- Reduced tertiary amides to intermediate enamines in a one-pot procedure.
- Reacted the in-situ generated enamines with sulfonyl azides.
Main Results:
- Successfully developed a one-pot protocol for N-sulfonylformamidine synthesis.
- Achieved moderate to good yields for the target compounds.
- Demonstrated the utility of Mo(CO)6 and TMDS in amide reduction.
Conclusions:
- The reported protocol provides an efficient route to N-sulfonylformamidines.
- This method offers a mild and practical approach for synthesizing valuable organic compounds.
- The catalytic reduction of amides to enamines is a key step in this transformation.
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