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One‐pot Annulation for Biaryl‐fused Monocarba‐ closo ‐dodecaborate through Aromatic B−H Bond Disconnection
Author(s) -
Akimoto Gaku,
Otsuka Mai,
Miyamoto Kazunori,
Muranaka Atsuya,
Hashizume Daisuke,
Takita Ryo,
Uchiyama Masanobu
Publication year - 2018
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201800053
Subject(s) - annulation , chemistry , medicinal chemistry , disconnection , combinatorial chemistry , organic chemistry , theology , philosophy , catalysis
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.