N-arylation heterocycle
In case different protomers of the 5-membered heterocycle exist, regioisomers are likely to be produced.
SMARTS: [c:1]B(O)O.[nH1;+0;r5;!$(n[#6]=[O,S,N]);!$(n~n~n);!$(n~n~c~n);!$(n~c~n~n):2]>>[c:1][n:2]
Conditions
Reactant 1: boronic acid.
Reactant 2: various 5-membered aromatic rings with NH and maximum two N.
R1: aryl.
References
Lam et. al., Tetrahedron Letters, 1998, 39, 2941-2944.
Other sources
Organic chemistry