Synthesis of 2,3-Bis(trifluoromethylseleno) Indoles through an Oxidative Copper-Mediated Domino Reaction

An oxidative copper-mediated double trifluorome-thylselenolation of terminal 2-alkynylanilines using [(bpy)-CuSeCF3](2) is reported, providing a moderately efficient and convenient approach to 2,3-bis(trifluoromethylseleno)indoles. Mechanistic studies show that a cascade sequence of oxidation, trifluoromethylselenolation, 5-endo-dig cyclization, and elimination is involved in this transformation.

Automated summary

An oxidative copper-mediated double trifluorome-thylselenolation of terminal 2-alkynylanilines using [(bpy)-CuSeCF3](2) is reported, providing a moderately efficient and convenient approach to 2,3-bis(trifluoromethylseleno)indoles. Mechanistic studies show that a cascade sequence of oxidation, trifluoromethylselenolation, 5-endo-dig cyclization, and elimination is involved in this transformation.