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  • 09월 05일 17시 이후 : 초록수정 불가능, 일정확인 및 검색만 가능

제120회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Regioselective Synthesis of Dihydrothiophenes and Thiophenes through the Rh-Catalyzed Transannulation of 1,2,3-Thiadiazoles with Alkenes

2017년 8월 3일 16시 07분 34초
ORGN.P-249 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
10월 20일 (금요일) 13:00~14:30
Organic Chemistry
저자 및
Jeong-Yu Son, Sang Hoon Han, Phil Ho Lee*
Department of Chemistry, Kangwon National University, Korea

Sulfur-containing five-membered heterocyclic compounds such as dihydrothiophenes and thiophenes represent key structural motifs due to their biological activities in natural products and pharmaceuticals. In addition, thiophene derivatives are very attractive compounds in the field of material science due to their peculiar structural rigidity and useful electronic properties. Thus, the development of synthetic methods for these core scaffolds has received considerable attention in contemporary chemistry. The regioselective introduction of a wide range of substituents onto dihydrothiophene and thiophene rings from readily available starting materials is required. In this study, the regioselective synthesis of a wide range of dihydrothiophenes was developed from the rhodium-catalyzed transannulation of 1,2,3-thiadiazoles with aliphatic, aromatic, and heteroaromatic alkenes. Tandem rhodium-catalyzed transannulation of 1,2,3-thiadiazoles with alkenes followed by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) oxidation was also demonstrated for the one-pot regioselective synthesis of various thiophenes. This method was employed to efficiently synthesize pentaoligomeric compounds consisting of three benzene and two dihydrothiophene rings. Advantages of the present method include a broad substrate scope, wide functional group compatibility, and high regioselectivity.This work was supported by the Human Resource Training Program for Regional Innovation and Creativity through the Ministry of Education and National Research Foundation of Korea (NRF-2015H1C1A1035955)