The serendipitous effect of KF in Ritter reaction: Photo-induced amino-alkylation of alkenes

Abstract

Summary: Ritter reaction has been recognized as an elegant strategy to construct the C−N bond. Its key feature is forming the carbocation for nucleophilic attack by nitriles. Herein, we report a complementary visible-light-induced three-component Ritter reaction of alkenes, nitriles, and α-bromo nitriles/esters, thereby providing mild and rapid access to various γ-amino nitriles/acids. Mechanistic studies indicated that traceless fluoride relay, transforming KF into imidoyl fluoride intermediate, is critical for the efficient reaction switch from atom transfer radical addition (ATRA) to the Ritter reaction. This approach to amino-alkylation of alkenes is chemoselective and operationally simple.

Keywords

• Chemistry
• Organic chemistry
• Organic synthesis