Ss. Labadie et E. Teng, INDOL-2-YLTRIBUTYLSTANNANE - A VERSATILE REAGENT FOR 2-SUBSTITUTED INDOLES, Journal of organic chemistry, 59(15), 1994, pp. 4250-4254
A general method for 2-substituted indoles via the palladium-catalyzed
coupling of indol-2-ylstannanes is described. (N-Methylindol-2-yl)tri
butylstannane (1) reacts with a variety of electrophiles under very mi
ld conditions: [N-tert-Butoxycarbonyl)indol-2-yl]tributylstannane (3)
is much less reactive in the coupling reactions and reacts only with c
ertain activated electrophiles. thylsilyl)ethoxy]methylindol-2-yl]trib
utylstannane (4) behaves similarly to 1 and the removal of the [(trime
thylsilyl)ethoxy]methyl group can be achieved with tetra-n-butylammoni
um fluoride in DMF in the presence of ethylenediamine.