Organic Letters· 2026Q1
Dual PCET-Enabled Chemoselective Decarboxylative Sulfinylation with N -Sulfinyl Phthalimides as Bench-Stable Sulfinyl Radical Precursors
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- Q1SCImago
- 2026year
Short summary
N-sulfinyl phthalimides enable direct decarboxylative sulfinylation of carboxylic acids to sulfoxides via a dual proton-coupled electron transfer (PCET) process, using sulfinyl radicals under mild conditions.
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Key points
- N-sulfinyl phthalimides serve as bench-stable precursors for sulfinyl radicals.
- A dual proton-coupled electron transfer (PCET) process enables direct decarboxylative sulfinylation of carboxylic acids to sulfoxides.
- The protocol demonstrates broad substrate scope and excellent chemoselectivity under mild conditions.
- Gram-scale reactions and late-stage functionalization of natural products and drugs were achieved.
- Mechanistic studies suggest a sulfinyl radical intermediate in the PCET pathway.
AI-generated from the title and abstract; the full text is not read.
Abstract
Abstract Herein, we disclose N-sulfinyl phthalimides as a new class of bench-stable and readily accessible sulfinyl radical precursors for the direct decarboxylative sulfinylation of carboxylic acids to sulfoxides via a dual proton-coupled electron transfer (PCET) process. This method demonstrated a remarkable substrate scope and excellent chemoselectivity across a diverse array of sulfoxide compounds under mild conditions. The synthetic utility and practicability of this robust protocol were further highlighted through gram-scale reactions, product derivatization, and late-stage functionalization of natural products and drugs. Mechanistic studies implicate a sulfinyl radical in the PCET pathway of this transformation. Moreover, a proof of concept for an asymmetric protocol by a merger of acridine photocatalysis and cobalt catalysis was also reported.
The authors' abstract, as published at the source. Organic Letters, 2026 · DOI ↗
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Field: Organic Chemistry
Organic ChemistryChemistry