Seminar

Seminar

Rh(III)-Catalyzed C-H Functionalization:Access to Novel Bioactive Molecules

  • POSTED DATE : 2018-11-01
  • WRITER : 관리자
  • HIT : 184
  • DATE : 2018-10-25
  • PLACE : 화학관 서병인강의실(330226호)

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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)

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Rh(III)-Catalyzed C-H Functionalization:

Access to Novel Bioactive Molecules

 

In Su Kim

School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea

insukim@skku.edu

 

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 >

  1. “Synthesis of 2-Benzazepines from Benzylamines and MBH Adducts Under Rhodium(III) Catalysis via C(sp2)-H Functionalization” ACS Catal. 2018, 8, 742–746.

  2. “Reactivity of Morita-Baylis-Hillamn Adducts in C-H Functionalization of (Hetero)aryl Nitrones: Access to Bridged Cycles and Carbazoles” Org. Lett. 2018, 20, 46324636.

  3. “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) \\

  4. “Reductive C2-Alkylation of Pyridine- and Quinoline-N-Oxides Using Wittig Reagents” Angew. Chem., Int. Ed. 2018, 57, 1273712740.