Condensing Agent to Form Redox-Active Esters (RAEs)

2-(1,3-Dioxoisoindolin-2-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate (= PITU, P3322) is used in the preparation of redox-active esters (RAEs) from carboxylic acids and N-hydroxyphthalimide (= NHPI). PITU rapidly converts carboxylic acids to RAEs in high yields at room temperature.¹) Due to its uronium moiety, it can suppress side reactions such as rearrangement to N-acylureas, which are typically observed with conventional carbodiimide condensing agents.¹) An example is the preparation of RAE from a carboxylic acid with DIPEA as base in CH2Cl2 at room temperature. RAEs serve as alkyl radical precursors in decarboxylative cross-coupling reactions. Furthermore, RAEs generated in situ from sodium carboxylates can be directly applied to electrochemical coupling reactions in one pot without further purification.²) An example is decarboxylative sp2–sp3 cross-coupling with NiCl2dme (cat.), dtbbpy (cat.), and NaI in DMA at room temperature under electrochemical conditions.

Related products

• TCI P3322 2226728-58-9 2-(1,3-Dioxoisoindolin-2-yl)-1,1,3,3-tetramethylisouronium Hexafluorophosphate

References

1. Ketones from Nickel‐Catalyzed Decarboxylative, Non‐Symmetric Cross‐Electrophile Coupling of Carboxylic Acid Esters. J. Wang et al., Angew. Chem. Int. Ed. 2019, 58, 12081. doi:10.1002/anie.201906000
2. One-Pot Electrochemical Nickel-Catalyzed Decarboxylative Sp2–Sp3 Cross-Coupling. T. Koyanagi et al., Org. Lett. 2019, 21, 816. doi:10.1021/acs.orglett.8b04090

Download TCI brochure Condensing Agent Enabling Redox Active Ester (RAEs) Formation (PDF)

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Source

• TCI Product Highlights: www.tcichemicals.com/ID/en/product/tci-topics/ProductHighlights_20260406
• TCI product page P3322: tcichemicals.com/ID/en/p/P3322

For research and laboratory use only, not for human consumption.