Journal
SCIENCE
Volume 363, Issue 6434, Pages 1429-+Publisher
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.aav3200
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Funding
- National Key R&D Program of China [2018YFB1501600, 2017YFA0303502]
- National Natural Science Foundation of China [21572212, 21732006, 51821006]
- Strategic Priority Research Program of CAS [XDB20000000, XDA21060101]
- HCPST [2017FXZY001]
- KY [2060000119]
- Supercomputing Center of USTC
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Most photoredox catalysts in current use are precious metal complexes or synthetically elaborate organic dyes, the cost of which can impede their application for large-scale industrial processes. We found that a combination of triphenylphosphine and sodium iodide under 456-nanometer irradiation by blue light-emitting diodes can catalyze the alkylation of silyl enol ethers by decarboxylative coupling with redox-active esters in the absence of transition metals. Deaminative alkylation using Katritzky's N-alkylpyridinium salts and trifluoromethylation using Togni's reagent are also demonstrated. Moreover, the phosphine/iodide-based photoredox system catalyzes Minisci-type alkylation of N-heterocycles and can operate in tandem with chiral phosphoric acids to achieve high enantioselectivity in this reaction.
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