Kang, Taeho; Erbay, Tugce G.; Xu, Kane L.; Gallego, Gary M.; Burtea, Alexander; Nair, Sajiv K.; Patman, Ryan L.; Zhou, Ru; Sutton, Scott C.; McAlpine, Indrawan J.; Liu, Peng; Engle, Keary M. published the artcile< Multifaceted Substrate-Ligand Interactions Promote the Copper-Catalyzed Hydroboration of Benzylidenecyclobutanes and Related Compounds>, Category: thiazole, the main research area is copper catalyzed hydroboration benzylidenecyclobutane diborane kinetics; chloro copper bisphosphinobenzene complex preparation crystal structure; mol structure chloro copper bisphosphinobenzene complex; 4-membered rings; Copper catalysis; benzylidenecyclobutanes; heterocycle; hydroborations; modified dppbz ligands; tertiary boronic esters.
A unified synthetic strategy to access tertiary four-membered carbo/heterocyclic boronic esters is reported. The use of a Cu(I) catalyst in combination with a modified 1,2-bis(diphenylphosphino)benzene (dppbz) ligand enables regioselective hydroboration of various trisubstituted benzylidenecyclobutanes and carbo/heterocyclic analogs. The reaction conditions are mild, and the method tolerates a wide range of medicinally relevant heteroarenes. The protocol can be conveniently conducted on a gram scale, and the tertiary boronic ester products undergo facile diversification into valuable targets. Reaction kinetics and computational studies indicate that the migratory insertion step is turnover-limiting and accelerated by electron-withdrawing groups on the dppbz ligand. Energy decomposition anal. calculations reveal that electron-deficient P-aryl groups on the dppbz ligand enhance the T-shaped π/π interactions with the substrate and stabilize the migratory insertion transition state.
ACS Catalysis published new progress about Aromatic hydrocarbons Role: SPN (Synthetic Preparation), PREP (Preparation) (benzylcyclobutane heteroarenes). 1003-32-3 belongs to class thiazole, and the molecular formula is C4H3NOS, Category: thiazole.
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica