Scheme 5. Scope of iodoarenes. Cross-coupling of iodoarenes and N-methyl indole catalyzed by the (P,N) gold complex. Unless otherwise stated, yields determined using calibrated GC-MS with n-dodecane as internal standard. Crystallographic structures of indoles 10 and 13 as inserts. Reaction conditions: 0.1 M of aryl iodide. ^aDTBP (2 eq.) instead of K₃PO₄. ^bDTBP (1 eq.) and N-methyl indole (1 eq.). ^cYields determined by NMR with n-dodecane as internal standard. ^dAll reagents weighted in air. ^eN-methyl indole (1 g), 2 mol% (MeDalphos)AuCI, 4.5 h, 1.3 M of aryl iodide. ^flsolated yield in parenthesis. ^gN-methyl indole (1 g), 1 mol% (MeDalphos)AuCI, overnight, 1.4 M of aryl iodide.