Copper-catalyzed C–N coupling of amides and nitrogen-containing heterocycles in the presence of cesium fluoride

Diamine ligands in copper-catalyzed reactions

“…71–75 This discovery has had a significant impact on the synthesis of natural products and pharmaceuticals ( vide infra ) and other catalyst systems have since been described by others. 19,22,26,76 …”

Protecting‐Group‐Free Total Synthesis of (−)‐Rhazinilam and (−)‐Rhazinicine using a Gold‐Catalyzed Cascade Cyclization

“…[21] Finally, saponification of the ester and subsequent lactamization furnished (À)-rhazinilam (1). Gratifyingly, crucial formation of the nine-membered lactam ring proceeded by copper-mediated intramolecular amidation [23] to furnish (À)-rhazinicine (2; Scheme 6). [2] In contrast to (À)-rhazinilam (1), it was a difficult challenge to construct the nine-membered lactam ring of (À)-rhazinicine (2) and leave the highly reactive N-acyl pyrrole functionality untouched.…”

“…[22] Then, the resultant carboxylic acid was converted into an amide by activation with CDI and subsequent treatment with ammonium hydroxide. Gratifyingly, crucial formation of the nine-membered lactam ring proceeded by copper-mediated intramolecular amidation [23] to furnish (À)-rhazinicine (2; Scheme 6). The physical and spectral properties, including optical rotation of synthetic 2, were identical to those reported for the natural product.…”

Ammonia synthons for the multicomponent assembly of complex γ-lactams

“…Although many methods, employing catalytic quantities of either copper (38)(39)(40) or palladium (41), have been described, these are often limited to substrates with little steric occlusion of the amide nitrogen. Use of these conditions with our substrate resulted in little or no observed product.…”