Catalyst-controlled site-selective N-H and C3-arylation of carbazoleviacarbene transfer reactions
A site-selective direct arylation reaction of carbazole and other N-heterocycles with diazo-naphthalen-2(1H)-ones has been developed. While Au(i)-NHC catalysts lead to selective C3-arylation, palladium acetate allows for selective N-H arylation, displaying complete site-selectivity each. To show the applicability of these arylation reactions, one-pot, two-fold diarylation reactions of carbazole were demonstrated.
Bahukhandi, Srishti Ballabh,Bera, Sourav Sekhar,Empel, Claire,Koenigs, Rene M.
supporting information
p. 6193 - 6196
(2021/06/30)
PdBr2-Catalyzed Acetal Formation of Carbonyl Compounds Using Diazophenanthrenequinone: Utility of 9,10-Phenanthrenedioxyacetal
We developed a new acetalization method of ketones and aldehydes under non-acidic conditions using diazophenanthrenequinone and PdBr2. The formed acetals that have a phenanthrene skeleton withstand under mild acidic conditions. Removal of acetals was successfully proceeded under strong acidic or oxidation conditions using aqueous ceric ammonium nitrate (CAN) to afford corresponding ketones and aldehydes.
Diastereoselective Palladium Catalyzed Carbenylative Amination of ortho-Vinylanilines with 3-Diazoindolin-2-ones
A diastereoselective palladium catalyzed carbenylative amination of ortho-vinylaniline with 3-diazoindolines-2-one have been accomplished for the synthesis of various tetrasubstituted indoline fused spirooxindole with good yields and diastereoselectivity. Notable features of the method include construction of two contiguous tetrasubstituted carbon stereocenters via C?N and C?C bond formation in single operation, wide functional group tolerance and high atom and step economy. Importantly, the present reaction was also extended to one-pot conversion of tosylhydrazones and ortho-vinylanilines to spirooxindole derivatives. (Figure presented.).