Journal
SYNLETT
Volume 27, Issue 5, Pages 754-758Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0035-1561320
Keywords
photoredox; catalysis; alkylation; C-H functionalization; quaternary carbon; flow reaction
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Funding
- National Science Foundation Graduate Research Fellowship Program [DGE 1256260]
- NIH-NIGMS [R01-GM096129]
- Alfred P. Sloan Foundation
- Camille Dreyfus Teacher-Scholar Award Program
- Eli Lilly
- Novartis
- University of Michigan
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The coupling of tertiary alkyl halides with electron-rich arenes is promoted by visible-light photoredox catalysis. Tris[2-phenylpyridinato-C-2,N]iridium(III) [Ir(ppy)(3)] was the optimal catalyst, enabling direct reduction of the halide from the excited state, and thereby eliminating the requirement for a stoichiometric electron donor. High yields were obtained when the aromatic component was used in excess, although equimolar amounts afforded only slightly diminished yields. The reaction tolerates a number of functional groups, including allyl, ester, amide, or carbamate. The efficiency of this reaction has been improved through demonstration of scale-up in flow, and a new substituted Ir(ppy)(3) derivative was isolated and characterized.
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