A Novel Synthesis of 2-Substituted Indole Derivatives: A Palladium Catalyzed Cross-coupling Reaction of Enol Triflate Derived from N-Methyl- 2-Indolone with (Alkenyl)tributylstannane and Acetylene

Title: A Novel Synthesis of 2-Substituted Indole Derivatives: A Palladium Catalyzed Cross-coupling Reaction of Enol Triflate Derived from N-Methyl- 2-Indolone with (Alkenyl)tributylstannane and Acetylene

Volume: 3 Issue: 11

Author(s): Akimori Wada, Masaki Shinmen, Jun'ichi Uenishi and Masayoshi Ito

Affiliation:

Keywords: Enol triflate, indolone, coupling reaction, alkenyl stannane, acetylene

Abstract: A novel method for a synthesis of N-methyl 2-substituted indole was developed by a palladium catalyzed cross-coupling reaction of an enol triflate derived from the N-methyl-2-indolone with (alkenyl)tributylstannanes and acetylenes in good to excellent yields. In addition, the enol triflate derived from lactam exhibited less reactivity with respect to cross-coupling reactions as compared with those of the enol triflates of 2-coumaranone and 2-indanone.

Cite this article as:

Wada Akimori, Shinmen Masaki, Uenishi Jun'ichi and Ito Masayoshi, A Novel Synthesis of 2-Substituted Indole Derivatives: A Palladium Catalyzed Cross-coupling Reaction of Enol Triflate Derived from N-Methyl- 2-Indolone with (Alkenyl)tributylstannane and Acetylene, Letters in Organic Chemistry 2006; 3 (11) . https://dx.doi.org/10.2174/157017806779117030