Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 16, Issue 1, Pages 87-96Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.202001304
Keywords
Bio-relevant scaffolds; 2-Arylbenzo[d]oxazole; 2-Arylbenzo[d]thiazole; C-H activation; ESI-MS guided k(H)/k(D) study
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Funding
- Department of Science and Technology, New Delhi
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Functionalization of 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 offers high yields and a broad substrate scope with respect to the coupling partners.
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.
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