Regio- and Stereoselective Allylindation of Alkynes Using InBr3 and Allylic Silanes: Synthesis, Characterization, and Application of 1,4-Dienylindiums toward Skipped Dienes
Yoshihiro Nishimoto,
Junyi Yi,
Tatsuaki Takata,
Akio Baba,
Makoto Yasuda
Affiliations
Yoshihiro Nishimoto
Frontier Research Base for Global Young Researchers Center for Open Innovation Research and Education (COiRE), Graduate School of Engineering, Osaka University; Osaka 565-0871, Japan
Junyi Yi
Department of Applied Chemistry, Graduate School of Engineering, Osaka University; Osaka 565-0871, Japan
Tatsuaki Takata
Department of Applied Chemistry, Graduate School of Engineering, Osaka University; Osaka 565-0871, Japan
Akio Baba
Department of Applied Chemistry, Graduate School of Engineering, Osaka University; Osaka 565-0871, Japan
Makoto Yasuda
Department of Applied Chemistry, Graduate School of Engineering, Osaka University; Osaka 565-0871, Japan
Regioselective anti-allylindation of alkynes was achieved using InBr3 and allylic silanes. Various types of alkynes and allylic silanes were applicable to the present allylindation. This sequential process used the generated 1,4-dienylindiums to establish novel synthetic methods for skipped dienes. The 1,4-dienylindiums were characterized by spectral analysis and treated with I2 to stereoselectively give 1-iodo-1,4-dienes. The Pd-catalyzed cross coupling of 1,4-dienylindium with iodobenzene successfully proceeded in a one-pot manner to afford the corresponding 1-aryl-1,4-diene.
