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4.4.7.2.8.1 Silaborative Dearomatization of Nitrogen Heterocycles

DOI: 10.1055/sos-SD-104-00395

Delvos, L. B.; Oestreich, M.Science of Synthesis Knowledge Updates, (20171151.

Silylboronic esters 233 react with electron-poor nitrogen heterocycles via silaborative dearomatization (Scheme 95).[‌123‌] Pyridines 232 with substituents in the 2- or 3-position undergo selective 1,4-reduction under palladium catalysis to generate dihydropyridines 234. (Chlorodimethylsilyl)pinacolborane (233, R1 = Cl) is generally more reactive and, in contrast to [dimethyl(phenyl)silyl]pinacolborane (233, R1 = Ph), tolerant of a methyl substituent in the 2-position.

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