Biswas, Sovan’s team published research in Angewandte Chemie, International Edition in 2021-09-27 | CAS: 100-70-9

Angewandte Chemie, International Edition published new progress about Alkenylation catalysts, stereoselective (regioselective). 100-70-9 belongs to class nitriles-buliding-blocks, name is Picolinonitrile, and the molecular formula is C6H4N2, Product Details of C6H4N2.

Biswas, Sovan published the artcileExpedient Synthesis of Bridged Bicyclic Nitrogen Scaffolds via Orthogonal Tandem Catalysis, Product Details of C6H4N2, the main research area is alkylidenenormorphan preparation diastereoselective regioselective; picolinamide gem dibromoalkene alkenylation amidation tandem palladium copper catalyst; alkenylation; bridged bicyclic nitrogen scaffolds; normorphan; remote functionalization; tandem catalysis.

Bridged nitrogen bicyclic skeletons I (R = t-Bu, Ph, cyclohexyl, 1-(benzenesulfonyl)-1H-indol-5-yl, etc.; R1 = H, methoxycarbonyl; R2 = H, Me; X = O, CH2, Et, (tert-butoxy)-formamidyl; Y = O, CH2, Et) have been accessed via unprecedented site- and diastereoselective orthogonal tandem catalysis from readily accessible reactants in a step economic manner. Directed Pd-catalyzed γ-C(sp3)-H olefination of aminocyclohexanes II (X = Y = CH2, Et) with gem-dibromoalkenes RCH=C(Br2), followed by a consecutive intramol. Cu-catalyzed amidation of the 1-bromo-1-alkenylated product III delivers the interesting normorphan skeleton. The tandem protocol can be applied on substituted aminocyclohexanes (X = Y = CH2) and aminoheterocycles II (X = O, (tert-butoxy)-formamidyl; Y = O), easily providing access to the corresponding substituted, aza- and oxa-analogs I. The Cu catalyst of the Ullmann-Goldberg reaction addnl. avoids off-cycle Pd catalyst scavenging by alkenylated reaction product IV. The picolinamides II directing group stabilizes the enamine of the 7-alkylidenenormorphans I, allowing further product V post functionalizations. Without Cu catalyst, regio- and diastereoselective Pd-catalyzed γ-C(sp3)-H olefination is achieved.

Angewandte Chemie, International Edition published new progress about Alkenylation catalysts, stereoselective (regioselective). 100-70-9 belongs to class nitriles-buliding-blocks, name is Picolinonitrile, and the molecular formula is C6H4N2, Product Details of C6H4N2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts