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제124회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Remote and Site-Selective Functionalization of Pyridinium Salts via Quinolinone Photocatalysis

2019년 9월 9일 10시 05분 37초
ORGN.P-451 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
10월 18일 (금요일) 11:00~12:30
Organic Chemistry
저자 및
Inwon Kim, Sungwoo Hong*
Department of Chemistry, Korea Advanced Institute of Science and Technology, Korea

Visible-light-induced site-selective heteroarylation of remote C(sp3)–H bonds has been accomplished through the design of N-alkoxyheteroarenium salts as both alkoxy radical sources and heteroaryl group sources. The alkoxy radical can be generated through the single electron reduction of N-alkoxypyridinium derivatives by a photoexcited quinolinone catalyst (Q1*). Subsequent radical translocation (1,5-HAT) of the O-centered radical forms a C-centered radical intermediate, which undergoes addition to the pyridinium substrate to achieve remote C(sp3)–H heteroarylation. This strategy provides a powerful platform for remote C(sp3)–H heteroarylation in a controllable and selective manner for the synthesis of a broad range of 4-heteroaryl alcohol products which have quaternary, tertiary, and secondary carbon centers. Also we developed a new approach to site-divergent pyridine functionalization that offers considerable advantages in both simplicity and efficiency. The site-selectivity can be switched from C2 to C4 by changing the radical coupling sources. Under standard reaction conditions, phosphinoyl radicals give access to C4 products, while carbamoyl radicals selectively give C2 products. These current methods are well suited for late-stage functionalization of complex bioactive molecules. References [1] I. Kim, G. Kang, K. Lee, B. Park, D. Kang, H. Jung, Y.-T. He, M.-H. Baik, S. Hong, J. Am. Chem. Soc. 2019, 141, 9239. [2] I. Kim, B. Park, G. Kang, J. Kim, H. Jung, H. Lee, M.-H. Baik, S. Hong, Angew. Chem. Int. Ed. 2018, 57, 15517. [3] I. Kim, M. Min, D. Kang, K. Kim, S. Hong, Org. Lett. 2017, 19, 1394. [4] Y. Kim, K. Lee, G. R. Mathi, I. Kim, S. Hong, Green Chem. 2019, 21, 2082. [5] F.-S. He, S. Ye, J. Wu, ACS Catal. 2019, 9, 8943.