Oxidative Imidation of Benzylic and Cycloalkane C(sp)-H Bond Donors Using -Aroyloxyquinuclidinium Salts and Nitriles under Photoredox Catalysis.

A series of -aroyloxyquinuclidinium salts were prepared and used as reagents to perform efficient three-component Ritter-Mumm-type oxidative C-H imidation of donors of 1° and 2° benzylic C-H bonds used as limiting reagents with nitriles as a source of imide nitrogen under photocatalytic conditions; these reagents also exhibit somewhat lower reactivity toward cycloalkanes.

Oxidative Trifluoroacetoxylation of 1°, 2°, and 3° Benzylic C(sp)-H Bond Donors Using -Trifluoroacetoxyquinuclidinium Salts under Photoredox Catalysis.

-Trifluoroacetoxyquinuclidinium trifluoroacetate was prepared from quinuclidine -oxide and (CFCO)O. Except for some electron-poor substrates, this reagent allows for the high-yielding oxidative trifluoroacetoxylation of 1°, 2°, and 3° benzylic C-H bonds under photocatalytic conditions. The trifluoroacetoxylation of an ibuprofen methyl ester allowed the selective functionalization of a 2° benzylic C-H bond.