Combining Indolizines and Isatins via Brønsted-Acid Catalyzed Friedel-Crafts Alkylation in Water

22 July 2020, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

The controlled mono-addition of indolizines to isatins under very mild conditions is described. The reaction occurs in water using diphenylphosphate (DPP) as catalyst and is dramatically accelerated by adding a surfactant (sodium dodecyl sulfate – SDS). Using this methodology, 19 new 3-hydroxy-3-indolizinyl-2-oxindoles scaffolds were synthesized (up to >99% yield). Notably, in organic solvents only bis-addition products were observed, in poor yields and in prolonged times. The very low solubility of the mono-addition product in water was determinant for the observed selectivity .

Keywords

indolizines
isatins
Friedel-Crafts alkylation
Bronsted acid catalysis
Single-addition
reactions in water
Green Chemistry

Supplementary materials

Title
Description
Actions
Title
SI Isa Ind water
Description
Actions

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