Selective C-C bond formation from rhodium-catalyzed C-H activation reaction of 2-arylpyridines with 3-aryl-2: H -azirines

Cited 0 time in webofscience Cited 0 time in scopus
8 Viewed 3 Downloaded
Title
Selective C-C bond formation from rhodium-catalyzed C-H activation reaction of 2-arylpyridines with 3-aryl-2: H -azirines
Author(s)
Yonghyeon Baek; Jinwoo Kim; Hyunseok Kim; Seung Jin Jung; Ho Ryu; Suyeon Kim; Jeong-Yu Son; Kyusik Um; Sang Hoon Han; Hyung Jin Seo; Juyoung Heo; Kooyeon Lee; Mu-Hyun Baik; Phil Ho Lee
Publication Date
2019-03
Journal
CHEMICAL SCIENCE, v.10, no.9, pp.2678 - 2686
Publisher
ROYAL SOC CHEMISTRY
Abstract
A novel method for the synthesis of acylmethyl-substituted 2-arylpyridine derivatives using 3-aryl-2H-azirines was developed by exploring a prototype reaction using DFT-calculations and carrying out targeted experiments guided by the calculated mechanism. 2H-Azirine was initially hypothesized to ring-open at the metal center to furnish familiar metal nitrene complexes that may undergo C-N coupling. Computational studies quickly revealed and prototype experimental work confirmed that neither the formation of the expected metal nitrene complexes nor the C-N coupling were viable. Instead, azirine ring-opening followed by C-C coupling was found to be much more favorable to give imines that readily underwent hydrolysis in aqueous conditions to form acylmethyl-substituted products. This new method was highly versatile and selective toward a wide range of substrates with high functional group tolerance. The utility of the new method is demonstrated by a convenient one-pot synthesis of biologically relevant heterocycles such as pyridoisoindole and pyridoisoqunolinone. © 2019 The Royal Society of Chemistry
URI
https://pr.ibs.re.kr/handle/8788114/5663
ISSN
2041-6520
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
Files in This Item:
c8sc05142a.pdfDownload

qrcode

  • facebook

    twitter

  • Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.
해당 아이템을 이메일로 공유하기 원하시면 인증을 거치시기 바랍니다.

Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.

Browse