C-N Heteroarene Cross-coupling

The parent pyrroles and indoles gave very poor yields (see Appendix, Section 5.12). However, Mederski [31], and Srirangam and co-workers [32] showed that N-arylation 

Xie and co-workers reported the N-arylation of imidazole in refluxing methanol in the presence of catalytic cuprous chloride or cupric acetate in air [26]. Yields are higher than the catalytic [Cu(OH) TM EDA 2C]l2 condition first introduced by Collman and co-workers [33a, b]. Similarly, the same conditions are applicable to phfhalamides [26], also with better yields than previously reported by Lam and co-workers [33c], Conversely, for aniline and sulfonamide substrates, Xie s conditions gave lower yield than Lam s conditions [33c]. Likewise, for basic amines, Batey s conditions [27] are superior. 

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