PALLADIUM-CATALYZED ALKENYLATION AND ALKYNYLATION OF POLYHALOARENES

Alkenylation of several polyhaloarenes proceeded in low to moderate yields. lodo groups could be reacted selectively in the presence of bromo groups; however, no more than two alkenyl groups could be introduced on contiguous, aromatic carbons. Alkynylation was more successful. Even hexa- and pentaalkynylarenes were obtainable in reasonable yields. Again, iodo groups could be reacted selectively in the presence of bromo groups. Convenient syntheses of a variety of 1,2,4,5-, 1,3,4,5-, and 1,2,4,6-tetrasubstituted aromatic compounds are possible by use of these reactions. © 1990, American Chemical Society. All rights reserved.