Journal
SYNLETT
Volume 32, Issue 17, Pages 1767-1771Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0040-1720388
Keywords
C(sp (3) )-H bond activation; photocatalysis; charge transfer; iron catalysis; alkylation; alkenes
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Funding
- NIGMS [GM125206]
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The FeCl (3) -catalyzed alkylation of nonactivated C(sp (3) )-H bonds is reported, involving photoinduced ligand-to-metal charge transfer and generation of chlorine radicals, which abstract hydrogen atoms from electron-rich C(sp (3) )-H bonds distal to electron-withdrawing functional groups. The resulting alkyl radicals react with electron-deficient olefins, and the catalytic cycle is closed through Fe(II) recombination and protodemetalation.
We report the FeCl (3) -catalyzed alkylation of nonactivated C(sp (3) )-H bonds. Photoinduced ligand-to-metal charge transfer at the iron center generates chlorine radicals that then preferentially abstract hydrogen atoms from electron-rich C(sp (3) )-H bonds distal to electron-withdrawing functional groups. The resultant alkyl radicals are trapped by electron-deficient olefins, and the catalytic cycle is closed by Fe(II) recombination and protodemetalation.
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