A Practical Protocol for Three-Component, One-Pot, Stepwise Sonogashira–Heterocyclization–Heck Couplings

Abstract

A three-component, one-pot, stepwise Sonogashira–­heterocyclization–Heck-coupling process was developed starting from either haloarenecarboxamides, halophenols or haloanilines, terminal alkynes and electron-deficient alkenes. Cyclic imidate-, benzofuran-, or indole-type products are obtained, respectively, in useful yields, being typically better than those obtained with isolation of the intermediate Sonogashira adducts. Very high 6-endo selectivity is maintained with imidate-type coupling products despite the presence of copper salts carried over from the Sonogashira coupling.

Key words

cyclization - Sonogashira reaction - Heck reactions - palladium - regioselectivity

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• 1 These authors contributed equally.

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