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    A mild light-driven protocol for the direct alkylation of phenols is reported. The process is driven by the photochemical activity of a halogen-bonded complex formed upon complexation of the in situ generated electron-rich phenolate anion with the α-iodosulfone. The reaction proceeds rapidly (10 min) under microfluidic conditions, delivering a wide variety of ortho-alkylated products (27 examples, up to 97% yield, >20:1 regioselectivity, on a gram scale), including densely functionalized bioactive phenol derivatives.


    Sara Cuadros, Cristian Rosso, Giorgia Barison, Paolo Costa, Marina Kurbasic, Marcella Bonchio, Maurizio Prato, Giacomo Filippini, Luca Dell'Amico. The Photochemical Activity of a Halogen-Bonded Complex Enables the Microfluidic Light-Driven Alkylation of Phenols. Organic letters. 2022 Apr 29;24(16):2961-2966

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    PMID: 35437017

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