Issue 33, 2015

Photochemically-induced C–C bond formation between tertiary amines and nitrones

Abstract

Photoexcited nitrones serve as excellent electron acceptors as well as radical acceptors in the presence of tertiary amines to give β-amino hydroxylamines via photochemically-induced direct sp3 C–H functionalization of the tertiary amines. The combined use of an organophotosensitizer and photoirradiation was highly effective in accelerating addition reactions. Several nitrones and tertiary amines were successfully utilized to give β-amino hydroxylamines in good yield. Highly regioselective generation of primary α-aminoalkyl radicals based on Lewis's stereoelectronic rule and diastereoselective addition reactions of primary α-aminoalkyl radicals with nitrones were successfully achieved. Furthermore, a highly diastereoselective reaction of an α-aminoalkyl radical with a chiral (E)-geometry-fixed α-alkoxycarbonylnitrone was performed.

Graphical abstract: Photochemically-induced C–C bond formation between tertiary amines and nitrones

Supplementary files

Article information

Article type
Paper
Submitted
23 Jun 2015
Accepted
14 Jul 2015
First published
14 Jul 2015

Org. Biomol. Chem., 2015,13, 8919-8924

Author version available

Photochemically-induced C–C bond formation between tertiary amines and nitrones

K. Itoh, R. Kato, D. Kinugawa, H. Kamiya, R. Kudo, M. Hasegawa, H. Fujii and H. Suga, Org. Biomol. Chem., 2015, 13, 8919 DOI: 10.1039/C5OB01277E

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