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Ruthenium (II) Catalyzed C(sp 2 )-H Bond Alkenylation of 2-Arylbenzo[d]oxazole and 2-Arylbenzo[d]thiazole with Unactivated Olefins.
- Source :
-
Chemistry, an Asian journal [Chem Asian J] 2021 Jan 04; Vol. 16 (1), pp. 87-96. Date of Electronic Publication: 2020 Dec 07. - Publication Year :
- 2021
-
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.<br /> (© 2020 Wiley-VCH GmbH.)
Details
- Language :
- English
- ISSN :
- 1861-471X
- Volume :
- 16
- Issue :
- 1
- Database :
- MEDLINE
- Journal :
- Chemistry, an Asian journal
- Publication Type :
- Academic Journal
- Accession number :
- 33230945
- Full Text :
- https://doi.org/10.1002/asia.202001304