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Selective Synthesis of Boron-Functionalized Indenes and Benzofulvenes by BCl₃-Promoted Cyclizations of ortho-Alkynylstyrenes.

ABSTRACT: A selective, metal-free synthesis of boron-functionalized indenes and benzofulvenes via BCl₃-mediated cyclization of o-alkynylstyrenes is described. The method allows precise control over product formation by adjusting reaction conditions. These borylated products were utilized in diverse C-B bond derivatizations and in the total synthesis of Sulindac, a nonsteroidal anti-inflammatory drug, demonstrating the versatility and practicality of the developed methodology for synthetic applications.

SUBMITTER: Humanes M

PROVIDER: S-EPMC11320658 | biostudies-literature | 2024 Aug

REPOSITORIES: biostudies-literature

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Selective Synthesis of Boron-Functionalized Indenes and Benzofulvenes by BCl3-Promoted Cyclizations of ortho-Alkynylstyrenes.

Humanes Marcos M Sans-Panadés Ester E Virumbrales Cintia C Milián Ana A Sanz Roberto R García-García Patricia P Fernández-Rodríguez Manuel A MA

Organic letters 20240728 31

A selective, metal-free synthesis of boron-functionalized indenes and benzofulvenes via BCl3-mediated cyclization of o-alkynylstyrenes is described. The method allows precise control over product formation by adjusting reaction conditions. These borylated products were utilized in diverse C-B bond derivatizations and in the total synthesis of Sulindac, a nonsteroidal anti-inflammatory drug, demonstrating the versatility and practicality of the developed methodology for syntheti ...[more]

PMID: 39069746

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