912551-99-6Relevant articles and documents
Generation and Cyclization of a Benzyne-Tethered Alkyllithium: Preparation of 4-Substituted Indans
Bailey, William F.,Longstaff, Sarah C.
, p. 432 - 433 (1998)
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Site-Selective C(sp3)–H Functionalization of Fluorinated Alkanes Driven by Polar Effects Using a Tungstate Photocatalyst
Fukuyama, Takahide,Nishikawa, Tomohiro,Ryu, Ilhyong
, p. 1424 - 1428 (2019/09/12)
The TBADT-catalyzed C(sp3)–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 α-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 α-C–H bonds. Radical polar effects in the SH2 transition states could explain this avoidance of α-C–H functionalization.