@article{pittir18775, volume = {12}, number = {20}, month = {October}, author = {XJ Wang and L Zhang and D Krishnamurthy and CH Senanayake and P Wipf}, title = {General solution to the synthesis of N-2-substituted 1,2,3-triazoles}, journal = {Organic Letters}, pages = {4632 -- 4635}, year = {2010}, url = {http://d-scholarship-dev.library.pitt.edu/18775/}, abstract = {The regioselective N-alkylation of 1,2,3-triazoles 1 - 6 was studied. Good to excellent N-2 selectivity and high chemical yields for N-2-substituted 4,5-dibromotriazoles 7 were obtained with 4,5-dibromo- and 4-bromo-5- trimethylsilyl-1,2,3-triazoles. These building blocks can be readily converted to 2-mono-, 2,4-di-, and 2,4,5-polysubstituted triazoles 10 - 15, providing a general, protective, group-free method for the synthesis of N-2-substituted triazoles. Observed regioselectivities can be rationalized by a combination of Frontier Molecular Orbital, steric, and electrostatic directing effects on the heterocyclic scaffolds. {\copyright} 2010 American Chemical Society.} }