meso-Hydroxylmethyl-1,3,5,7-tetramethylBODIPY: A Visible-Light Photoremovable Protective Group for Carboxyl Groups

Abstract

A meso-BODIPY-type photoremovable protecting group for carboxyl group is developed. BODIPYs are well-known for brilliant color, favorable to reaction monitoring and purification. meso-BODIPY esters are achieved via esterification in 44–89% yields, while deprotection is fulfilled under irradiation of blue LED bulb in the presence of photocatalyst and organic hydrogen donor in 43–95% yields. This method is applicable to a variety of acids, such as aromatic, heteroaromatic, alkyl, α,β-unsaturated carboxylic acids, etc. Our BODIPY-deprotective condition is almost neutral that both methyl and tert-butyl esters are compatible.

Key words

BODIPY - protective group for carboxyl group - ethidine - visible-light - photocatalyst

Publication History

Received: 25 July 2024

Accepted after revision: 12 September 2024

Accepted Manuscript online:
12 September 2024

Article published online:
08 October 2024

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