The C–H activated controlled mono- and di-olefination of arenes in ionic liquids at room temperature

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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Ruthenium (II) Catalyzed C(sp²)−H Bond Alkenylation of 2‐Arylbenzo[d]oxazole and 2‐Arylbenzo[d]thiazole with Unactivated Olefins

Pipaliya

Seth

Chakraborti

2020

Chemistry An Asian Journal

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Recent advancements in applications of ionic liquids in synthetic construction of heterocyclic scaffolds: A spotlight

Dhameliya

Nagar

Bhakhar

et al. 2022

Journal of Molecular Liquids

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Rh(III)-catalyzed ortho-C–H bond functionalization of 2-arylquinoxalines with vinyl arenes

Chary

Aashritha

Sridhar

et al. 2021

Tetrahedron Letters

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The C–H activated controlled mono- and di-olefination of arenes in ionic liquids at room temperature

Abstract: The controlled mono- and di-olefination of arenes was first realized at room temperature through C–H bond activation in ionic liquids.

Cited by 5 publications

References 63 publications

Ruthenium (II) Catalyzed C(sp²)−H Bond Alkenylation of 2‐Arylbenzo[d]oxazole and 2‐Arylbenzo[d]thiazole with Unactivated Olefins

Ruthenium (II) Catalyzed C(sp²)−H Bond Alkenylation of 2‐Arylbenzo[d]oxazole and 2‐Arylbenzo[d]thiazole with Unactivated Olefins

Recent advancements in applications of ionic liquids in synthetic construction of heterocyclic scaffolds: A spotlight

Rh(III)-catalyzed ortho-C–H bond functionalization of 2-arylquinoxalines with vinyl arenes

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The C–H activated controlled mono- and di-olefination of arenes in ionic liquids at room temperature

Abstract: The controlled mono- and di-olefination of arenes was first realized at room temperature through C–H bond activation in ionic liquids.

Cited by 5 publications

References 63 publications

Ruthenium (II) Catalyzed C(sp2)−H Bond Alkenylation of 2‐Arylbenzo[d]oxazole and 2‐Arylbenzo[d]thiazole with Unactivated Olefins

Ruthenium (II) Catalyzed C(sp2)−H Bond Alkenylation of 2‐Arylbenzo[d]oxazole and 2‐Arylbenzo[d]thiazole with Unactivated Olefins

Recent advancements in applications of ionic liquids in synthetic construction of heterocyclic scaffolds: A spotlight

Rh(III)-catalyzed ortho-C–H bond functionalization of 2-arylquinoxalines with vinyl arenes

Contact Info

Product

Resources

About

Ruthenium (II) Catalyzed C(sp²)−H Bond Alkenylation of 2‐Arylbenzo[d]oxazole and 2‐Arylbenzo[d]thiazole with Unactivated Olefins

Ruthenium (II) Catalyzed C(sp²)−H Bond Alkenylation of 2‐Arylbenzo[d]oxazole and 2‐Arylbenzo[d]thiazole with Unactivated Olefins