Photocatalytic decarboxylative alkylations mediated by triphenylphosphine and sodium iodide

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 b...

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Published inScience (American Association for the Advancement of Science) Vol. 363; no. 6434; pp. 1429 - 1434
Main Authors Fu, Ming-Chen, Shang, Rui, Zhao, Bin, Wang, Bing, Fu, Yao
Format Journal Article
LanguageEnglish
Published United States The American Association for the Advancement of Science 29.03.2019
Subjects
Alkylation
Catalysis
Catalysts
Channeling
Chemical reactions
Chromophores
Coordination compounds
Electron transfer
Enantiomers
Esters
Ethers
Iodides
Irradiation
Metal complexes
Organic chemistry
Organic light emitting diodes
Phosphine
Photoredox catalysis
Radiation
Reagents
Salts
Sodium
Sodium iodide
Transition metals
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Summary: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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ISSN:0036-8075
1095-9203
DOI:10.1126/science.aav3200