[2179-92-2] · C13H27NSn · Cyanotributylstannane · (MW 316.07)
(reagent for cyanation of halides; can add to aldehydes; catalyst for halosilane substitution)
Alternate Name: tributyltin cyanide.
Solubility: sol common org solvents.
Form Supplied in: colorless solid.
Handling, Storage, and Precautions: hygroscopic, but stable under a dry atmosphere. Both cyano and alkyltin compounds are highly toxic.
Cyanation of vinyl or aryl halides is effectively catalyzed by palladium(0) complexes. The reaction can be applied to the synthesis of cyano homologs of nucleosides (eq 1),4 nucleoside bases,5 and cis-dihydrodiols derived from arenes.6
Aryl, vinyl, and tertiary alkyl acid halides can be cyanated by the reagent to give acyl cyanides in good yields (eq 2).2 Primary or secondary alkyl acid halides react further to afford acyl cyanide dimers.
The three-component coupling of aryl halides, cyanotributylstannane, and isocyanides takes place in the presence of palladium(0) to yield iminoacyl cyanides in moderate yields.7
Cyanohydrins are obtained by the reaction of cyanotributylstannane with aldehydes. Although a chiral titanium catalyst did not effect any asymmetric induction,8a good 1,2-diastereoselectivity was achieved in the reaction with a-amino aldehydes.8b
A catalytic amount of cyanotributylstannane facilitates the substitution of silyl chlorides by Grignard reagents.9
Masato Tanaka & Toshiyasu Sakakura
National Institute of Materials and Chemical Research, Tsukuba, Japan