SELECTIVE REDUCTIONS .14. FAST REACTION OF ARYL BROMIDES AND IODIDES WITH LITHIUM ALUMINUM HYDRIDE IN TETRAHYDROFURAN . A SIMPLE, CONVENIENT PROCEDURE FOR HYDROGENOLYSIS OF ARYL BROMIDES AND IODIDES

Unactivated aromatic bromides are reduced quite rapidly and quantitatively to the corresponding hydrocarbons by lithium aluminum hydride in refluxing tetrahydrofuran. Iodides are reduced at a reasonable rate even at room temperature. The ease of reduction of the different halogens, as indicated by rate studies, follows the order I > Br > Cl > F. Iodo and bromo substituents can be selectively removed in the presence of chloro substituents. This provides a convenient synthetic procedure for debromination and deiodination of aryl halides where this is required in synthetic operations. © 1969, American Chemical Society. All rights reserved.