Huisgen Cu-catalyzed 1,4 substitution
Alcohols can be directly converted to hazides under Mitsunobu conditions. Additional step: substitution of halogen or hydroxy group (Mitsunobu) with azide. Stereochemistry at secondary halides/alcohols need to be considered.
SMARTS: [CH0;$(C-[#6]):1]#[CH1:2].[C;H1,H2;A;!$(C=O):3]-[*;#17,#35,#53,OH1]>>[C:1]1=[C:2]-N(-[C:3])-N=N-1
Conditions
Reactant 1: nitrile.
Reactant 2: alkyl halide or alcohol.
R1: aryl, alkyl. R2: aliphatic carbon. X: Cl, Br, I, OH.
References
Chengzhi, Org. Lett., 2000, 1959-1961, 2.
Thompson, J. Org. Chem., 1993, 5886-5888, 58.