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Photoinduced C(sp3)?N Bond Cleavage Leading to the Stereoselective Syntheses of Alkenes |
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| Authors: | Ze-Kun Yang Ning-Xin Xu Dr Chao Wang Prof?Dr Masanobu Uchiyama |
| Institution: | 1. Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-0033 Japan
Cluster for Pioneering Research (CPR), Advanced Elements Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako-shi, Saitama, 351-0198 Japan These authors contributed equally to this work.;2. Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-0033 Japan These authors contributed equally to this work.;3. Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-0033 Japan |
| Abstract: | Herein we report a versatile Mizoroki–Heck-type photoinduced C(sp3)?N bond cleavage reaction. Under visible-light irradiation (455 nm, blue LEDs) at room temperature, alkyl Katritzky salts react smoothly with alkenes in a 1:1 molar ratio in the presence of 1.0 mol % of commercially available photoredox catalyst without the need for any base, affording the corresponding alkyl-substituted alkenes in good yields with broad functional-group compatibility. Notably, the E/Z-selectivity of the alkene products can be controlled by an appropriate choice of photoredox catalyst. |
| Keywords: | alkenes amines C?N bond cleavage Mizoroki–Heck reaction photoredox catalysis |