Cu‐Mediated Synthesis of Indolines and Dihydroisoquinolinones through Arylperfluoroalkylation of Unactivated Alkenes

Abstract

The copper‐mediated fluroalkylation/cyclization of N‐allyl anilines has been described using fluoroalkyl iodides as fluoroalkylation reagents for the first time. The reaction provides an efficient and direct access to 3‐fluoroalkyl indolines in moderate to good yields with unactivated double bonds as the radical acceptor. This protocol combines a simple experimental procedure with low‐costing fluoroalkylated sources and excellent functional group tolerance.

Fluoroalkyl Iodides in Fluoroalkylative Difunctionalization of C−C Multiple Bonds

“…In contrast to several mild protocols for the synthesis of fluoroalkylated oxindoles, the related synthesis of perfluoroalkylated indolines, 1,2,3,4‐tetrahydroquinolines 31 a , and 2,3‐dihydrobenzofurans 31 b have been reported under relatively harsh conditions, including under Pd‐catalysis at 100 °C, [149] or using stoichiometric amounts of copper at 120 °C (Scheme 39). [150] For the copper mediated approach, if the N‐protecting group (R 2 ) is benzoyl, the cyclization occur at this side, leading to the 1(2H)‐isoquinolinone derivative 32 (Scheme 39) (only 4 examples). Pd‐catalysis was also employed for the synthesis of pyrrolo[1,2‐a]indoles through fluoroalkylation‐arylation of N‐homoallylindols [151] .…”