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Issue 9, 2019
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Selective C–C bond formation from rhodium-catalyzed C–H activation reaction of 2-arylpyridines with 3-aryl-2H-azirines

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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.

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

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Supplementary files

Article information


Submitted
17 Nov 2018
Accepted
05 Jan 2019
First published
08 Jan 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 2678-2686
Article type
Edge Article

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

Y. Baek, J. Kim, Hyunseok Kim, S. J. Jung, H. Ryu, S. Kim, J. Son, K. Um, S. H. Han, H. J. Seo, J. Heo, K. Lee, M. Baik and P. H. Lee, Chem. Sci., 2019, 10, 2678
DOI: 10.1039/C8SC05142A

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