Copper-catalyzed synthesis of five-membered heterocycles via double C–N bond formation: an efficient synthesis of pyrroles, dihydropyrroles, and carbazoles

Diamine ligands in copper-catalyzed reactions

“…Li 143,144 and Buchwald 145 have both delineated a route to substituted pyrroles based on the Cu-catalyzed double alkenylation of amides with 1,4-diiodo-1,3-dienes which are available from the zirconium- 146 or titanium-mediated 147 coupling of two alkynes (Scheme 23). …”

Transition Metal-Mediated Synthesis of Monocyclic Aromatic Heterocycles

“…Thus, Li et al reported the Cu(I)-catalyzed double alkenylation of amides with 1,4-diiodo-1,3-dienes 3-268 to obtain tri- and tetrasubstituted N -acylpyrroles 3-269a (Scheme 247). 403 Alkylcarbamates can also be employed in this reaction, however, in this case stoichiometric amounts of CuI are required. Recently, this methodology was extended to aromatic amines.…”

Pd‐Catalyzed C‐H/N‐H Arylation: One‐Pot Synthesis of Indolo[1, 2‐f]phenanthridines

“…In addition, Pd‐catalyzed coupling reactions of the C2‐H or N‐H of indoles with aryl halides have been successfully achieved. Recently, our groups reported Cu‐catalyzed C−N couplings of 2,2’‐diiodobiphenyl with amide to afford carbazoles . We envisioned that a tandem reaction of generally available indole derivatives and 2,2’‐dihalobiphenyl would afford indole‐fused phenanthridines through indole N−H and C2(sp2)‐H arylation.…”