Three- and Four-Component Syntheses of 3-Arylmethylindoles by Microwave-Assisted One-Pot Heck Isomerization–Fischer Indolization (Alkylation) (HIFI and HIFIA) Sequences

Dedicated to Prof. Dr. Rolf Gleiter on the occasion of his 80^th birthday.

Abstract

Initiated by Heck isomerization of aryl bromides and allyl alcohols, the intermediate 3-arylpropanal is readily transformed into 3-arylmethylindoles by Fischer indole synthesis in a consecutive three-component fashion in moderate to good yields. This Heck isomerization–Fischer indolization (HIFI) sequence can be readily concatenated into a four-component Heck isomerization–Fischer indolization–alkylation (HIFIA) synthesis affording products in good to excellent yields.

Key words

alkylations - Heck reactions - microwave-assisted synthesis - multicomponent reactions - indoles

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