Pipaliya, Bhavin V. ; Seth, Kapileswar ; Chakraborti, Asit K. (2021) Ruthenium (II) Catalyzed C(sp 2 )−H Bond Alkenylation of 2‐Arylbenzo[ d ]oxazole and 2‐Arylbenzo[ d ]thiazole with Unactivated Olefins Chemistry – An Asian Journal, 16 (1). pp. 87-96. ISSN 1861-4728
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Official URL: http://doi.org/10.1002/asia.202001304
Related URL: http://dx.doi.org/10.1002/asia.202001304
Abstract
Functionalization of the bio-relevant heterocycles 2-arylbenzo[d]oxazole and 2-arylbenzo[d]thiazole has been achieved through Ru(II)-catalyzed alkenylation with unactivated olefins leading to selective formation of the mono-alkenylated products. This approach has a broad substrate scope with respect to the coupling partners, affords high yields, and works for gram scale synthesis using a readily available Ru-based catalyst. Mechanistic studies reveal a C−H activation pathway for the dehydrogenative coupling leading to the alkenylation. However, the results of the ESI-MS-guided deuterium kinetic isotope effect studies indicate that the C−H activation stage may not be the rate-determining step of the reaction. The use of a radical scavenging agent such as TEMPO did not show any detrimental effect on the reaction outcome, eliminating the possibility of the involvement of a free-radical pathway.
Item Type: | Article |
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Source: | Copyright of this article belongs to John Wiley & Sons, Inc |
ID Code: | 129447 |
Deposited On: | 16 Nov 2022 09:48 |
Last Modified: | 16 Nov 2022 09:48 |
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