Synthesis of Bench-Stable N- Quaternized Ketene N , O -Acetals and Preliminary Evaluation as Reagents in Organic Synthesis.

Autor:	McConnell DL; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Blades AM; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Rodrigues DG; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Keyes PV; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Sonberg JC; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Anthony CE; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Rachad S; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Simone OM; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Sullivan CF; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Shapiro JD; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Williams CC; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Schafer BC; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Glanzer AM; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Hutchinson HL; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Thayaparan AB; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Krevlin ZA; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Bote IC; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Haffary YA; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Bhandari S; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Goodman JA; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Majireck MM; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States.
Jazyk:	angličtina
Zdroj:	The Journal of organic chemistry [J Org Chem] 2021 Sep 17; Vol. 86 (18), pp. 13025-13040. Date of Electronic Publication: 2021 Sep 09.
DOI:	10.1021/acs.joc.1c01764
Abstrakt:	N -Quaternized ketene N , O -acetals are typically an unstable, transient class of compounds most commonly observed as reactive intermediates. In this report, we describe a general synthetic approach to a variety of bench-stable N -quaternized ketene N , O -acetals via treatment of pyridine or aniline bases with acetylenic ethers and an appropriate Brønsted or Lewis acid (triflic acid, triflimide, or scandium(III) triflate). The resulting pyridinium and anilinium salts can be used as reagents or synthetic intermediates in multiple reaction types. For example, N -(1-ethoxyvinyl)pyridinium or anilinium salts can thermally release highly reactive O -ethyl ketenium ions for use in acid catalyst-free electrophilic aromatic substitutions. N -(1-Ethoxyvinyl)-2-halopyridinium salts can be employed in peptide couplings as a derivative of Mukaiyama reagents or react with amines in nucleophilic aromatic substitutions under mild conditions. These preliminary reactions illustrate the broad potential of these currently understudied compounds in organic synthesis.
Databáze:	MEDLINE
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