The Photochemical Activity of a Halogen-Bonded Complex Enables the Microfluidic Light-Driven Alkylation of Phenols.

Sara Cuadros, Cristian Rosso, Giorgia Barison, Paolo Costa, Marina Kurbasic, Marcella Bonchio, Maurizio Prato, Giacomo Filippini, Luca Dell'Amico

Organic letters 2022 Apr 29

filter terms:

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.

Citation

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