Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2020, Issue 10, Pages 1424-1428Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201901135
Keywords
C-H functionalization; Photocatalysis; Radical reactions; Synthetic methods
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Funding
- JSPS [19H02722]
- MEXT [2707, JP15H05850]
- Grants-in-Aid for Scientific Research [19H02722] Funding Source: KAKEN
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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.
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