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제120회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Cross-Coupling Reaction of 8-Methylquinolines with Allylic Alcohols Under Rhodium(III)-Catalysis

2017년 8월 31일 15시 42분 52초
ORGN.P-437 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
10월 20일 (금요일) 13:00~14:30
Organic Chemistry
저자 및
Saegun Kim, IN SU KIM1,*
University of Pharmacy, Sungkyunkwan University, Korea
1College of Pharmacy / Department of Pharmacy, Sungkyunkwan University, Korea

The rhodium(III)-catalyzed cross-coupling reaction of 8-methylquinolines with a range of allylic alcohols in water is described. This approach leads to the synthesis of various γ-quinolinyl carbonyl compounds, which are synthetically useful precursors for the construction of bioactive tetrahydroquinoline and azasteroid derivatives. Induced by the need to streamline the synthesis of valuable building blocks and complex molecules, the transition-metal catalyzed C–H bond activation has evolved as an important field in organic synthesis. It has attracted tremendous interest in developing cross-coupling reactions at low cost without the use of stoichiometric amounts of organometallic reagents. In particular, C(sp2)–H functionalization has been studied to a greater extent, whereas less research attention has been paid to the activation of C(sp3)–H bonds. In this area, sp3 C–H functionalizations have been executed with the assistance of a range of chelating auxiliaries such as amides, carboxylic acids, oximes, N-heterocycles, etc. In particular, 8-methylquinolines have been found to be good substrates for sp3 C–H functionalization due to their ability to form cyclometalated complexes. However, sp3 C–H alkylation of 8-methylquinolines has rarely been explored. Although the catalytic C–H bond functionalizations provide atom economy, which constitutes a great contribution to the cross-coupling reaction, most of these reactions have been carried out in organic solvents. In continuation of our Rh(III)-catalyzed sp2 and sp3 C–H alkylations, we herein report for the first time the C(sp3)–H alkylation of 8-methylquinolines with allylic alcohols in water as a green solvent.