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  • 09월 10일 16시 이후 : 초록수정 불가능, 일정확인 및 검색만 가능

제124회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Selective formation of γ-lactams via C–H amidation enabled by tailored iridium catalysts

2019년 9월 16일 18시 13분 19초
KCS.O-1 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
목 09시 : 45분
KCS - Oral Presentation for 2019 DOW Korea Award
저자 및
Seung Youn Hong, Yoonsu Park, Yeongyu Hwang, Yeong Bum Kim, Mu-Hyun Baik*, Sukbok Chang*
Department of Chemistry, Korea Advanced Institute of Science and Technology, Korea

The direct amidation of C–H bonds to obtain nitrogen-containing heterocycles is a highly desirable reaction because it will open the door to many new applications in chemical synthesis. Although tremendous progress has been made, our current ability to prepare heterocycles via such direct C–H functionalization is limited. We have developed a novel methodology that employs Ir-based catalysts and dioxazolone substrates to access short-lived Ir-nitrenoid complexes, which are key intermediates in the efficient construction of γ-lactams through direct C−H bond amidation. Stoichiometric studies with robust carbonylnitrene precursor, 1,4,2-dioxazol-5-ones, suggest that the insertion of C−H into metal-nitrenoid moiety is possible and mechanistic clues from the initial proof-of-concept studies further enabled the rational design of efficient and versatile catalysts that allows for the straightforward amidations of various sp3- and sp2 C−H bonds with exceptional selectivity leading to lactam products. The power of this new method is demonstrated in the successful late-stage functionalization of bio-active molecules with amino acid derivatives to produce molecules that are highly sought after for pharmaceutical and other applications in synthesis.