Photoinduced, copper-catalyzed alkylation of amides with unactivated secondary alkyl halides at room temperature.

摘要: The development of a mild and general method for the alkylation amides with relatively unreactive alkyl halides (i.e., poor substrates SN2 reactions) is an ongoing challenge in organic synthesis. We describe herein versatile transition-metal-catalyzed approach: particular, photoinduced, copper-catalyzed monoalkylation primary amides. A broad array aryl (as well as lactam 2-oxazolidinone) couple unactivated secondary (and hindered primary) bromides iodides using single set comparatively simple conditions: inexpensive CuI catalyst, no separate added ligand, C–N bond formation at room temperature. compatible variety functional groups, such olefin, carbamate, thiophene, pyridine, it has been applied to synthesis opioid receptor antagonist. range mechanistic observations, including reactivity stereochemical studies, are consistent coupling pathway that inclu...