Regioselective Morita-Baylis-Hillman Reaction with N-Alkylpyridinium Salts as Electrophiles

28 February 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Morita-Baylis-Hillman reaction employing N-alkylpyridinium salts as electrophiles has been developed. The reaction is promoted by DBU, which acts both as a catalyst activating the electron-poor olefin as well as a base. The transformation delivers a broad range of α-(hydropyridine)vinyl esters, ketones, and sulfones. The dearomatization of N-alkylquinolinium salts occurs regioselctively at the C-2 position, whereas N-alkylpyridinium salts undergo addition at the C-4 position.

Keywords

Morita-Baylis-Hillman
N-alkylpyridinium
dearomatization
regioselectivity

Supplementary materials

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Supporting information
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experimental procedures, compound characterization data, and copies of NMR spectra for products
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