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A practical preparation of bicyclic boronates via metal-free heteroatom-directed alkenyl sp²-C‒H borylation.

ABSTRACT: Bicyclic boronates play critical roles in the discovery of functional materials and antibacterial agents, especially against deadly bacterial pathogens. Their practical and convenient preparation is in high demand but with great challenge. Herein, we report an efficient strategy for the preparation of bicyclic boronates through metal-free heteroatom-directed alkenyl sp²-C‒H borylation. This synthetic approach exhibits good functional group compatibility, and the corresponding boronates bearing halides, aryls, acyclic and cyclic frameworks are obtained with high yields (43 examples, up to 95% yield). Furthermore, a gram-scale experiment is conducted, and downstream transformations of the bicyclic boronates are pursued to afford natural products, drug scaffolds, and chiral hemiboronic acid catalysts.

SUBMITTER: Peng PY

PROVIDER: S-EPMC10447525 | biostudies-literature | 2023 Aug

REPOSITORIES: biostudies-literature

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A practical preparation of bicyclic boronates via metal-free heteroatom-directed alkenyl sp2-C‒H borylation.

Peng Pei-Ying PY Zhang Gui-Shan GS Gong Mei-Ling ML Zhang Jian-Wei JW Liu Xi-Liang XL Gao Dingding D Lin Guo-Qiang GQ Li Qing-Hua QH Tian Ping P

Communications chemistry 20230823 1

Bicyclic boronates play critical roles in the discovery of functional materials and antibacterial agents, especially against deadly bacterial pathogens. Their practical and convenient preparation is in high demand but with great challenge. Herein, we report an efficient strategy for the preparation of bicyclic boronates through metal-free heteroatom-directed alkenyl sp2-C‒H borylation. This synthetic approach exhibits good functional group compatibility, and the corresponding boronate ...[more]

PMID: 37612464

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