α-Silyl amines as electron donors: application in synthetic organic chemistry

• Published in: Russian chemical bulletin Vol. 73; no. 4; pp. 761 - 786
• Main Authors: Lazareva, N. F., Lazarev, I. M.
• Format: Journal Article
• Language: English
• Published: New York Springer US 01-04-2024; Springer Nature B.V
• Subjects: Amines; Carbon; Cations; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Electron transfer; Inorganic Chemistry; Ionization potentials; Organic Chemistry; Organosilicon compounds; Oxidation; Reviews; Single electrons; α-silyl amines; single-electron transfer; radical cation; reactions of α-silyl amines; C-centered α-aminoalkyl radical
• ISSN: 1066-5285; 1573-9171
• DOI: 10.1007/s11172-024-4191-0

α-Silyl amines are unique organosilicon compounds containing a geminal NCH
2
Si fragment. The introduction of a triorganylsilyl group at α-position to the nitrogen atom decreases the ionization potential and promotes an electron transfer with the formation of the corresponding radical cation. The review discusses methods for generating α-silyl amine radical cations (electrochemical, chemical, and photochemical) and also generalizes and systematizes reactions of α-silyl amines which include the stage of single-electron transfer. Single-electron oxidation of neutral α-silyl amines is a simple and efficient approach to highly reactive C-centered α-aminoalkyl radicals, which are very attractive from the point of view of synthetic organic chemistry in terms of the formation of new carbon—carbon bonds.