Title: | Site-Selective C(sp(3))-H Functionalization of Fluorinated Alkanes Driven by Polar Effects Using a Tungstate Photocatalyst |
Authors: | Fukuyama, Takahide Nishikawa, Tomohiro Ryu, Ilhyong 應用化學系 Department of Applied Chemistry |
Keywords: | C-H functionalization;Photocatalysis;Radical reactions;Synthetic methods |
Issue Date: | 1-Jan-1970 |
Abstract: | The TBADT-catalyzed C(sp(3))-H functionalization of perfluorophenyl- and perfluoroalkyl-substituted alkanes was studied to determine how the fluorous substituents affect site-selectivity. Alkylation of alkyl-substituted perfluorobenzene avoids alpha-C-H bonds, unlike their alkylbenzene counterparts, allowing site-selective functionalization of C-H bonds remote to the aromatic ring. Alkylation of alkanes having a perfluoroalkyl group also avoided alpha-C-H bonds. Radical polar effects in the S(H)2 transition states could explain this avoidance of alpha-C-H functionalization. |
URI: | http://dx.doi.org/10.1002/ejoc.201901135 http://hdl.handle.net/11536/152895 |
ISSN: | 1434-193X |
DOI: | 10.1002/ejoc.201901135 |
Journal: | EUROPEAN JOURNAL OF ORGANIC CHEMISTRY |
Begin Page: | 0 |
End Page: | 0 |
Appears in Collections: | Articles |