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

ABSTRACT: 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.

SUBMITTER: Cuadros S

PROVIDER: S-EPMC9062880 | biostudies-literature | 2022 Apr

REPOSITORIES: biostudies-literature

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

Cuadros Sara S Rosso Cristian C Barison Giorgia G Costa Paolo P Kurbasic Marina M Bonchio Marcella M Prato Maurizio M Filippini Giacomo G Dell'Amico Luca L

Organic letters 20220419 16

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 <i>in situ</i> 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 ...[more]

PMID: 35437017

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