Here we report a catalytic method for the intermolecular anti-Markovnikov hydroamination of unactivated alkenes using primary and secondary sulfonamides. These reactions occur at room temperature under visible light irradiation and are jointly catalyzed by an iridium(III) photocatalyst, a dialkyl phosphate base, and a thiol hydrogen atom donor. Reaction outcomes are consistent with the intermediacy of an N-centered sulfonamidyl radical generated via proton-coupled electron transfer activation of the sulfonamide N-H bond. Studies outlining the synthetic scope (>60 examples) and mechanistic features of the reaction are presented.
Here we report a catalytic method for the intermolecular anti-Markovnikov hydroamination of unactivated alkenes using primary and secondary n class="Chemical">sulfonamides. These reactions occur at room temperature under visible light irradiation and are jointly catalyzed by an iridium(III) photocatalyst, a dialkyl phosphate base, and a thiolhydrogen atom donor. Reaction outcomes are consistent with the intermediacy of an N-centered sulfonamidyl radical generated via proton-coupled electron transfer activation of the sulfonamideN-H bond. Studies outlining the synthetic scope (>60 examples) and mechanistic features of the reaction are presented.
Authors: Kuo Zhao; Kenji Yamashita; Joseph E Carpenter; Trevor C Sherwood; William R Ewing; Peter T W Cheng; Robert R Knowles Journal: J Am Chem Soc Date: 2019-05-23 Impact factor: 15.419
Authors: David C Miller; Jacob M Ganley; Andrew J Musacchio; Trevor C Sherwood; William R Ewing; Robert R Knowles Journal: J Am Chem Soc Date: 2019-10-14 Impact factor: 15.419
Authors: Carla M Morton; Qilei Zhu; Hunter Ripberger; Ludovic Troian-Gautier; Zi S D Toa; Robert R Knowles; Erik J Alexanian Journal: J Am Chem Soc Date: 2019-08-12 Impact factor: 15.419