TCFH–NMI: Direct Access to N-Acyl Imidazoliums for Challenging Amide Bond Formations | Zendy

Gregory L. Beutner | Zendy; Ian S. Young | Zendy; Merrill L. Davies | Zendy; Matthew Hickey | Zendy; Hyunsoo Park | Zendy; Jason M. Stevens | Zendy; Qingmei Ye | Zendy

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TCFH–NMI: Direct Access to N-Acyl Imidazoliums for Challenging Amide Bond Formations

Author(s) -

Gregory L. Beutner,

Ian S. Young,

Merrill L. Davies,

Matthew Hickey,

Hyunsoo Park,

Jason M. Stevens,

Qingmei Ye

Publication year - 2018

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.8b01591

Subject(s) - chemistry , hexafluorophosphate , reagent , stereocenter , amide , reactivity (psychology) , nucleophile , primary (astronomy) , combinatorial chemistry , peptide bond , medicinal chemistry , organic chemistry , ionic liquid , catalysis , enantioselective synthesis , pathology , medicine , alternative medicine , physics , astronomy , enzyme

Challenging couplings of hindered carboxylic acids with non-nucleophilic amines to form amide bonds can be accomplished in high yields, and in many cases, with complete retention of the adjacent stereogenic centers using the combination of N, N, N', N'-tetramethylchloroformamidinium hexafluorophosphate (TCFH) and N-methylimidazole (NMI). This method allows for in situ generation of highly reactive acyl imidazolium ions, which have been demonstrated to be intermediates in the reaction. The reagent delivers high reactivity similar to acid chlorides with the ease of use of modern uronium reagents.

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