S. Labadie, Edmond Teng
Jul 1, 1994
Citations
0
Influential Citations
63
Citations
Journal
Journal of Organic Chemistry
Abstract
A general method for 2-substituted indoles via the palladium-catalyzed coupling of indol-2-ylstannanes is described. (N-Methylindol-2-yl)tributylstannane (1) reacts with a variety of electrophiles under very mild conditions. [N-tert-Butoxycarbonyl)indol-2-yl]tributylstannane (3) is much less reactive in the coupling reactions and reacts only with certain activated electrophiles. [N-[[(Trimethylsilyl)ethoxy]methylindol-2-yl]tributylstannane (4) behaves similarly to 1 and the removal of the [(trimethylsilyl)ethoxy]methyl group can be achieved with tetra-n-butylammonium fluoride in DMF in the presence of ethylenediamine