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Palladium-Catalyzed Markovnikov-Selective Hydroselenation of N-Vinyl Lactams with Selenols Affording N,Se-Acetals

Author:
Tamai, Taichi, Yoshikawa, Megumi, Higashimae, Shinya, Nomoto, Akihiro, Ogawa, Akiya
Source:
Journal of organic chemistry 2016 v.81 no.1 pp. 324-329
ISSN:
1520-6904
Subject:
acidity, catalysts, catalytic activity, chemical reactions, chemical structure, lactams, organic chemistry, palladium, regioselectivity
Abstract:
The highly regioselective hydroselenation of N-vinyl lactams has been revealed to successfully afford the corresponding N,Se-acetals as Markovnikov adducts. In the case of terminal N-vinyl lactams, Markovnikov-selective hydroselenation proceeds efficiently in the absence of any catalyst (or additive), owing to the acidity of the selenols. In contrast, the self-promoted hydroselenation is inefficient with internal N-vinyl lactams. In the presence of palladium diacetate (Pd(OAc)₂), however, the desired hydroselenation of internal N-vinyl lactams proceeds efficiently to afford the corresponding N,Se-acetals.
Agid:
5505439