Nickel-Catalyzed Reversible Functional Group Metathesis between Aryl Nitriles and Aryl Thioethers
We describe a new functional group metathesis between aryl nitriles and aryl thioethers. The catalytic system nickel/dcype is essential to achieve this fully reversible transformation in good to excellent yields. Furthermore, the cyanide- and thiol-free reaction shows high functional group tolerance and great efficiency for the late-stage derivatization of commercial molecules. Finally, synthetic applications demonstrate its versatility and utility in multistep synthesis.
Delcaillau, Tristan,Boehm, Philip,Morandi, Bill
supporting information
p. 3723 - 3728
(2021/04/07)
Thioether-Directed Selective C4 C-H Alkenylation of Indoles under Rhodium Catalysis
A thioether-directed Rh(III)-catalyzed C4 selective C-H alkenylation of indoles via the formation of 5-membered metallacycle intermediates is reported. This protocol allows a wide functional group compatibility and broad substrate scope. The directing group can be readily removed or transformed into other functional groups after the C-H functionalization event. The catalytic method is also applicable to related heterocyclic systems involving benzo[b]thiophene and benzo[b]furan scaffolds.