Aminosulfonylation of Rhodium Carbene via Ylide Formation and 1,4-Sulfonyl Rearrangement

Area of Science:

• Organic Chemistry
• Synthetic Methodology

Background:

• Sulfonylation reactions are crucial in organic synthesis.
• Developing novel reagents and protocols for difunctionalization is an active research area.

Purpose of the Study:

• To report a novel difunctionalization protocol using pyridin-2-yl benzenesulfonates.
• To achieve the simultaneous installation of a sulfonyl group and a pyridone moiety.

Main Methods:

• Utilized pyridin-2-yl benzenesulfonates as sulfonylation reagents.
• Employed oxy-pyridinium ylide chemistry.
• Conducted Density Functional Theory (DFT) calculations to elucidate the mechanism.

Main Results:

• Developed an effective protocol for installing both sulfonyl and pyridone groups in a single step.
• Demonstrated the utility of pyridin-2-yl benzenesulfonates in difunctionalization.
• DFT calculations suggested a reaction pathway involving ylide formation, tautomerism, and rearrangement.

Conclusions:

• Pyridin-2-yl benzenesulfonates are effective reagents for a novel difunctionalization reaction.
• The developed protocol offers an efficient route to molecules containing sulfonyl and pyridone functionalities.
• The reaction mechanism likely involves ylide intermediates and a sulfonyl group migration.