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Sulfoximine Assisted C-H Activation and Annulation via Vinylene Transfer: Access to Unsubstituted Benzothiazines.

ABSTRACT: In this study, we report the synthesis of unsubstituted 1,2-benzothiazines through a redox-neutral Rh(III)-catalyzed C-H activation and [4+2]-annulation of S-aryl sulfoximines with vinylene carbonate. Notably, the introduction of an N-protected amino acid ligand significantly enhances the reaction rate. The key aspect of this redox-neutral process is the utilization of vinylene carbonate as an oxidizing acetylene surrogate and an efficient vinylene transfer agent. This vinylene carbonate enables the cyclization with the sulfoximine motifs, successfully forming a diverse array of 1,2-benzothiazine derivatives in moderate to good yields. Importantly, this study highlights the potential of Rh(III)-catalyzed C-H activation and [4+2]-annulation reactions for the synthesis of optically pure 1,2-benzothiazines with high enantiomeric purity.

SUBMITTER: Kondalarao K

PROVIDER: S-EPMC10343390 | biostudies-literature | 2023 Jun

REPOSITORIES: biostudies-literature

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Sulfoximine Assisted C-H Activation and Annulation via Vinylene Transfer: Access to Unsubstituted Benzothiazines.

Kondalarao Koneti K Sau Somratan S Sahoo Akhila K AK

Molecules (Basel, Switzerland) 20230627 13

In this study, we report the synthesis of unsubstituted 1,2-benzothiazines through a redox-neutral Rh(III)-catalyzed C-H activation and [4+2]-annulation of S-aryl sulfoximines with vinylene carbonate. Notably, the introduction of an N-protected amino acid ligand significantly enhances the reaction rate. The key aspect of this redox-neutral process is the utilization of vinylene carbonate as an oxidizing acetylene surrogate and an efficient vinylene transfer agent. This vinylene carbonate enables ...[more]

PMID: 37446676

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