Site-selectivity in TBADT-photocatalyzed C(sp3)–H Functionalization of Saturated Alcohols and Alkanes

Site-selectivity in C(sp3)–H functionalization of aliphatic alcohols and alkanes was studied using the decatungstate anion as a photocatalyst. In the case of aliphatic alcohols, C–H bond α to the hydroxy group was preferentially functionalized. The α-site-selectivity is rationalized by polar effects...

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Bibliographic Details
Published in:Chemistry letters 2018-01, Vol.47 (2), p.207-209
Main Authors: Fukuyama, Takahide, Yamada, Keiichi, Nishikawa, Tomohiro, Ravelli, Davide, Fagnoni, Maurizio, Ryu, Illhyong
Format: Article
Language:English
Subjects:
Alcohol
Aliphatic alcohols
Aliphatic compounds
Alkanes
Hydrogen bonds
Selectivity
Steric effects
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Summary:Site-selectivity in C(sp3)–H functionalization of aliphatic alcohols and alkanes was studied using the decatungstate anion as a photocatalyst. In the case of aliphatic alcohols, C–H bond α to the hydroxy group was preferentially functionalized. The α-site-selectivity is rationalized by polar effects imparted by the hydroxy group in the SH2 transition states. In contrast, C–H functionalization of alkanes was largely affected by steric effects.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.171068