We report herein a redox neutral visible light-induced regioselective C(sp)-H imidation of electron-rich arenes and heteroarenes using conceptually designed redox-active 1 as a source of the N-centered imidyl radical. Structurally diverse aromatic imides were obtained in moderate to good yields. This methodology has been successfully employed for the late stage imidation of complex molecules and has also been applied towards the formal total synthesis of the marine natural products carpatamides A, B and D. It has further been shown that the generated imides can easily be converted to the corresponding anilines directly.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1039/d2ob02040h | DOI Listing |
J Am Chem Soc
June 2006
Department of Applied Chemistry Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464-8603, Japan.
Highly substituted iodobenzenes were efficiently and regioselectively synthesized from readily available 1,6-diynes via two-step process consisting of silver-catalyzed Csp-H iodination and subsequent ruthenium-catalyzed [2 + 2 + 2] cycloaddition of resultant iododiynes. Some of the obtained iodobenzenes were subjected to palladium-catalyzed C-C bond-forming reactions such as Mizoroki-Heck reaction, Sonogashira reaction, and Suzuki-Miyaura coupling, giving highly conjugated molecules.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!