Huisgen disubstitution alkyne
Not regioselective: in case the alkyne is non-symmetrically substituted both regioisomers are likely to be formed. Additional step: substitution of halogen or hydroxy group (Mitsunobu) with azide. Stereochemistry at secondary halides/alcohols need to be considered.
SMARTS: [CH0;$(C-[#6]):1]#[CH0;$(C-[#6]):2].[C;H1,H2;A;!$(C=O):3]-[*;#17,#35,#53,OH1]>>[C:1]1=[C:2]-N=NN(-[C:3])-1
Conditions
Reactant 1: alkyne.
Reactant 2: alkyl halide or alcohol.
R1, R2: aryl, alkyl. R3: aliphatic carbon. X: Cl, Br, I, OH.
References
Chengzhi, Org. Lett., 2000, 1959-1961, 2.
Thompson, J. Org. Chem., 1993, 5886-5888, 58.