Buchwald-Hartwig
SMARTS: [Cl,Br,I][c;$(c1:[c,n]:[c,n]:[c,n]:[c,n]:[c,n]:1):1].[N;$(NC)&!$(N=*)&!$([N-])&!$(N#*)&!$([ND3])&!$([ND4])&!$(N[c,O])&!$(N[C,S]=[S,O,N]),H2&$(Nc1:[c,n]:[c,n]:[c,n]:[c,n]:[c,n]:1):2]>>[c:1][N:2]
Conditions
Reactant 1: aryl halide.
Reactant 2: primary or secondary amine.
R1: H, alkyl. R2: alky, aryl. X: Cl, Br, I.
References
Guram, A. S.; Buchwald, S. L. J. Am. Chem. Soc., 1994, 116, 7901–7902.
Paul, F.; Patt, J.; Hartwig, J. F. J. Am. Chem. Soc., 1994, 116, 5969–5970.
Other sources
Organic chemistry
Wikipedia