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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 34, Number 1
BKCSDE 34(1)
January 20, 2013 

Functionalization of Organotrifluoroborates via Cu-Catalyzed C-N Coupling Reaction
Jung-Hyun Lee,a, Heejin Kim, Taejung Kim, Jung Ho Song, Won-Suk Kim*, Jungyeob Ham*
Organotrifluoroborate, Potassium N-heterobiaryltrifluoroborates, Cu-catalyzed C-N coupling, Chan-Lam coupling, N-Heterobiarene
Potassium N-heterobiaryltrifluoroborates were successfully prepared via a selective Cu-catalyzed C-N coupling reaction. The BF3K moiety was well tolerated under the reaction conditions involving CuI and dimethylethylenediamine (DMEDA) in the presence of DMSO. The Pd-catalyzed Suzuki-Miyaura cross couplings of potassium N-heterobiaryltrifluoroborates with bromoarenes were studied to prepare the N-heterotriaryl compounds. Moreover, homocoupling, iodination, and hydroxylation of potassium N-heterobiaryltrifluoroborates provided the corresponding products in high yields.
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