One-pot Annulation for Biaryl-fused Monocarba-closo-dodecaborate through Aromatic B-H Bond Disconnection

Chemistry, an Asian Journal
Gaku AkimotoMasanobu Uchiyama

Abstract

We have developed a one-pot annulation reaction of monocarba-closo-dodecaborate with cyclic diaryliodonium salts to afford biaryl-fused derivatives. Aryl functionalities are introduced at both the 1-carbon and unreactive ortho-boron vertices of the "σ-aromatic" carborane cage without the need for pre-functionalization. DFT calculations revealed that the palladium-catalyzed C-B bond-formation step in this process proceeds through a concerted metalation-deprotonation (CMD)-type pathway for the B-H bond disconnection on the aromatic cage, though such bonds are generally regarded as hydridic.

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Citations

Mar 26, 2019·Chemistry : a European Journal·Junichiro KanazawaMasanobu Uchiyama
Oct 28, 2019·Chemistry, an Asian Journal·Wai Yeung Raymond WongKe-Wen Tang

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