CAS 94790-35-9, Cat. No EN300-7361941
Reagent for peptide synthesis and other nucleophiles coupling
Chloro-N,N,N′,N′-tetramethylformamidinium hexafluorophosphate (TCHF) is a reliable reagent-activator in tandem with N-methylimidazole (NMI) that usually applies to reactions with weak nucleophiles. It is a white solid that is soluble in common organic solvents1. The reaction conditions are soft, but moderate heating in some cases is required2. Sterically and electronically diverse anilines, and heteroaryl amines, can be coupled in reasonable reaction times and good yields, even when the reactions are run under air. Also, this coupling technique is perfect for the hindered carboxylic group3.
Synonyms: tetramethylchloroformamidinium hexafluorophosphate; chloro-N,N,N′,N′-tetramethylformamidinium hexafluorophosphate; TCHF
Selected publications
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Tetramethylchloroformamidinium Hexafluorophosphate.
Lebel H. Encyclopedia of Reagents for Organic Synthesis 2021, 1-5. DOI: 10.1002/047084289X.rn02314
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TCFH–NMI: Direct Access to N-Acyl Imidazoliums for Challenging Amide Bond Formations.
Beutner G.; Young I.; Davies M.; Hickey M.; Park H.; Stevens J.; Ye Q. Org Lett 2018, 20 (14), 4218–4222. DOI: 10.1021/acs.orglett.8b01591
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Beyond Amide Bond Formation: TCFH as a Reagent for Esterification.
Luis N.; Chung K.; Hickey M.; Lin Z.; Beutner G.; Vosburg D. Org Lett 2023. DOI: 10.1021/acs.orglett.3c01611