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Ru(II)-Catalyzed Regioselective C-N Bond Formation on Benzothiazoles Employing Acyl Azide as an Amidating Agent.

ABSTRACT: A Ru(II)-catalyzed regioselective direct ortho-amidation of 2-aryl benzo[d]thiazoles employing acyl azides as a nitrogen source has been accomplished. This approach utilizes the efficiency of benzothiazole as a directing group and the role of acyl azide as an effective amidating agent toward C-N bond formation, thereby evading the general Curtius rearrangement. The protocol highlights significant functional group tolerance, single-step, and external oxidant-free conditions, with the release of only innocuous molecular nitrogen as the byproduct. The reaction mechanism and the intermediates associated with this selective Ru-catalyzed reaction have been investigated using ESI-MS. The protocol also aided in the construction of ortho-amidated β-carbolines, unveiling another class of fluorescent molecules.

SUBMITTER: John SE

PROVIDER: S-EPMC8756580 | biostudies-literature | 2022 Jan

REPOSITORIES: biostudies-literature

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Ru(II)-Catalyzed Regioselective C-N Bond Formation on Benzothiazoles Employing Acyl Azide as an Amidating Agent.

John Stephy Elza SE Bora Darshana D Dhiman Vivek V Tokala Ramya R Samanthula Gananadhamu G Shankaraiah Nagula N

ACS omega 20211227 1

A Ru(II)-catalyzed regioselective direct <i>ortho</i>-amidation of 2-aryl benzo[<i>d</i>]thiazoles employing acyl azides as a nitrogen source has been accomplished. This approach utilizes the efficiency of benzothiazole as a directing group and the role of acyl azide as an effective amidating agent toward C-N bond formation, thereby evading the general Curtius rearrangement. The protocol highlights significant functional group tolerance, single-step, and external oxidant-free conditions, with th ...[more]

PMID: 35036791

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