Cu-Catalyzed Three-Component Regio- and Stereoselective 1,5-Difunctionalizations of Unactivated Vinyl Cyclopropanes with Fluoroalkyl Iodides and TMSY (Y = CN, N3, NCS).

Key Points

• To develop a copper-catalyzed method for 1,5-difunctionalization of unactivated vinyl cyclopropanes using fluoroalkyl iodides.
• Conducted a copper-catalyzed three-component reaction using fluoroalkyl iodides and TMSY.
• Explored a broad range of substrates to evaluate regioselectivity and stereoselectivity.
• Performed mechanistic studies using DFT calculations to understand the underlying reaction pathway.
• Synthesis of structurally diverse fluoroalkylated alkenyl nitriles was achieved with high regioselectivity.
• 29 out of 40 products exhibited ≥10:1 E/Z selectivity, highlighting the success in stereoselectivity.
• Mechanistic studies indicated a radical pathway involving a SET/XAT process.