Herein, we report the phosphonylacylation of alkenes via visible-light-induced N-heterocyclic carbene (NHC) catalysis to afford a series of gamma-ketophosphonates in moderate to good yields. This protocol features mild conditions, free of photocatalyst, and good compatibility of functional groups. The excited Breslow enolate intermediate was proposed to undergo single-electron transfer with oxime phosphonate to generate the corresponding ketyl radical and phosphonyl radical.
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Univ Toronto, Dept Chem, Davenport Chem Res Labs, 80 St George St, Toronto, ON M5S 3H6, CanadaUniv Toronto, Dept Chem, Davenport Chem Res Labs, 80 St George St, Toronto, ON M5S 3H6, Canada
Liang, Qiuming
Song, Datong
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Univ Toronto, Dept Chem, Davenport Chem Res Labs, 80 St George St, Toronto, ON M5S 3H6, CanadaUniv Toronto, Dept Chem, Davenport Chem Res Labs, 80 St George St, Toronto, ON M5S 3H6, Canada
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Nicolaus Copernicus Univ Torun, Fac Chem, Gagarin St 7, PL-87100 Torun, PolandNicolaus Copernicus Univ Torun, Fac Chem, Gagarin St 7, PL-87100 Torun, Poland
Dzieszkowski, Krzysztof
Rafinski, Zbigniew
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Nicolaus Copernicus Univ Torun, Fac Chem, Gagarin St 7, PL-87100 Torun, PolandNicolaus Copernicus Univ Torun, Fac Chem, Gagarin St 7, PL-87100 Torun, Poland
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Kanazawa Univ, Div Pharmaceut Sci, Grad Sch Med Sci, Kakuma Machi, Kanazawa, Ishikawa 9201192, JapanKanazawa Univ, Div Pharmaceut Sci, Grad Sch Med Sci, Kakuma Machi, Kanazawa, Ishikawa 9201192, Japan
Nagao, Kazunori
Ohmiya, Hirohisa
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Kanazawa Univ, Div Pharmaceut Sci, Grad Sch Med Sci, Kakuma Machi, Kanazawa, Ishikawa 9201192, JapanKanazawa Univ, Div Pharmaceut Sci, Grad Sch Med Sci, Kakuma Machi, Kanazawa, Ishikawa 9201192, Japan