1,3-Diamine Formation from an Interrupted Hofmann-Löffler Reaction: Iodine Catalyst Turnover through Ritter-Type Amination

Abstract

An iodine-catalyzed Ritter-type amination of nonactivated C-H bonds is presented enabling the formation of 1,3-α-tertiary diamines. A sulfamidyl radical serves as the promoter in a guided tertiary C-H iodination through an exclusive 1,6-HAT process. The subsequent Ritter reaction furnishes the C-N bond and establishes an unprecedented concept for catalyst turnover in iodine redox catalysis. The general robustness of the methodology, including broad functional group tolerance, was demonstrated for 24 different 1,3-diamine derivatives, which were synthesized in yields of 42%-99%.