Differentially protected benzenediboronic acids: divalent cross-coupling modules for the efficient synthesis of boron-substituted oligoarenes.
On the basis of the boron-masking strategy, new divalent cross-coupling modules have been designed for the efficient synthesis of boron-substituted oligoarenes. The modules, i.e., monoprotected o-, m-, and p-benzenediboronic acid derivatives, undergo highly selective Suzuki-Miyaura coupling with sp2 iodides, bromides, chlorides, and triflates, affording coupling products in which the protected boronyl groups are left intact.
Noguchi
Hiroyoshi
H
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Kyoto 615-8510, Japan.
Shioda
Takayuki
T
Chou
Chih-Ming
CM
Suginome
Michinori
M
D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D006846:Hydrocarbons, Halogenated / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
D001896:Boron Compounds; D001897:Boronic Acids; D006846:Hydrocarbons, Halogenated; D008698:Mesylates; C010686:benzeneboronic acid