제 목 : Rh(III)-Catalyzed C-H Functionalization:Access to Novel Bioactive Molecules
연 사 : 김인수 교수님(성균관대학교 약학과)
일 시 : 2018년 10월 25일(목) 오후 4시 30분
장 소 : 화학관 2층 서병인강의실(330226호실)
Rh(III)-Catalyzed C-H Functionalization:
Access to Novel Bioactive Molecules
In Su Kim
School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea
With considerable progress in medicinal chemistry, the construction of heterocycles has receiveed increasing attention in the past decades. In particular, N-heterocycles are widely found to be biologically relevant scaffolds of natural products, pharmaceuticals, agrochemicals, and functional materials. In this context, the directing group-assisted N-heterocycle synthesis via C-H bond functionalization is highly attractive in pharmaceutical industry. Thus, we recently reported the construction of N-heterocycles via the Rh(III)-catalyzed C-H functionalization followed by intramolecular cyclization. Moreover, our group recently focused on the synthesis and biological evaluation of N-heterocycles such as xanthones, chromones, indoles, azaindoles, indolines, acridines, and indolidinones, and etc.
We herein describe a brief summary of our recent works on the synthesis of 2-benzazepines,1 bridged bicycles,2 carbazoles,2 and 2-naphthols3 using Morita-Balyis-Hillman (MBH) adducts as novel C-H allylation sources under Rh(III) catalysis. Additionally, we present the unexpected reactivity and selectivity of phosphonium salts (Wittig reagents) on the reductive C2-alkylation of pyridine and quinoline N-oxides, leading C2-alkylated pyridines and quinolines.4 The ability to alkylate pyridines and quinolines is also important for their further development as pharmaceuticals and agrochemicals, and for other purposes.
< References >
“Synthesis of 2-Benzazepines from Benzylamines and MBH Adducts Under Rhodium(III) Catalysis via C(sp2)-H Functionalization” ACS Catal. 2018, 8, 742–746.
“Reactivity of Morita-Baylis-Hillamn Adducts in C-H Functionalization of (Hetero)aryl Nitrones: Access to Bridged Cycles and Carbazoles” Org. Lett. 2018, 20, 4632–4636.
“One-pot Synthesis of 2-Naphthols Using Nitrones and MBH Adducts via Decarboxylative N-O Bond Cleavage” Org. Chem. Front. 2018, 5, in press. (selected as Cover Page of OCF) \\
“Reductive C2-Alkylation of Pyridine- and Quinoline-N-Oxides Using Wittig Reagents” Angew. Chem., Int. Ed. 2018, 57, 12737–12740.