B-N bond formation through palladium-catalyzed, microwave-assisted cross-coupling of nitrogen compounds with iodo-dodecaborate

Substituted undecahydrido- closo -dodecaborates [B 12 H 11 NR 2 ] 2− have potential use in materials and drugs, but have presented a synthetic challenge. Microwave-assisted palladium-catalyzed amination of iodo-dodecaborate [B 12 H 11 I] 2− allows mild and reproducible formation of B-N bonds with aromatic amines, HN-containing heteroaromatics, and amides. The reaction allows general access to amides, reproducible reactions to dodecaborate-substituted anilines, and, for the first time, the substitution of dodecaborate with HN-containing heterocycles. A method is described which allows the synthesis of nitrogen-substituted hydridododecaborate clusters through Pd-catalyzed cross-coupling.