Rhodium-Catalyzed ortho-Bromination of O-Phenyl Carbamates Accelerated by a Secondary Amide-Pendant Cyclopentadienyl Ligand
It has been established that a newly developed cyclopentadienyl rhodium(III) [CpARhIII] complex, bearing an acidic secondary amide moiety on the Cp ring, is able to catalyze the ortho-bromination of O-phenyl carbamates with N-bromosuccinimide (NBS) at room temperature. The presence of the acidic secondary amide moiety on the CpA ligand accelerates the bromination by the hydrogen bond between the acidic NH group of the CpA ligand and the carbonyl group of NBS.
Tanaka, Jin,Shibata, Yu,Joseph, Anton,Nogami, Juntaro,Terasawa, Jyunichi,Yoshimura, Ryo,Tanaka, Ken
supporting information
p. 5774 - 5779
(2020/05/08)
Ligand-assisted copper-catalyzed oxidative cross-coupling of simple phenols with formamides for the synthesis of carbamates
An oxidative approach for the synthesis of phenyl carbamates has been achieved by ligand-assisted copper-catalyzed cross-dehydrogenative coupling (CDC) of phenols with formamides. The direct coupling of simple phenols with mono- and dialkyl formamides pro
Palladium catalyzed C-H functionalization of O-arylcarbamates: Selective ortho -bromination using NBS
A series of cyclometalated palladium complexes derived from O-phenylcarbamates has been synthesized by the reaction of the respective carbamates with Pd(OAc)2 in the presence of acids, CF 3CO2H, CF3SO3/sub
John, Alex,Nicholas, Kenneth M.
p. 5600 - 5605
(2012/07/30)
High-yielding, versatile, and practical [Rh(III)Cp*]-catalyzed ortho bromination and iodination of arenes
We report a uniquely high-yielding, general, and practical ortho bromination and iodination reaction of different classes of aromatic compounds. This reaction occurs by Rh(III)-catalyzed C-H bond activation methodology and is therefore the first example of the application of this cationic catalyst for C-Br and C-I bond formation.
Schroeder, Nils,Wencel-Delord, Joanna,Glorius, Frank
supporting information; experimental part
p. 8298 - 8301
(2012/06/29)
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