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

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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
DOI
10.1039/c8sc05142a
ISSN
2041-6520
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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