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Visible Light-Driven Strain-Increase Ring Contraction Allows the Synthesis of Cyclobutyl Boronic Esters

Research output: Contribution to journalArticle

Original languageEnglish
JournalAngewandte Chemie - International Edition
Early online date8 Jan 2020
DOIs
DateAccepted/In press - 8 Jan 2020
DateE-pub ahead of print (current) - 8 Jan 2020

Abstract

There are a limited number of ring contraction methodologies which convert readily available 5‐membered rings into strained 4‐membered rings. Here we report a photo‐induced radical‐mediated ring contraction of 5‐membered ring alkenyl boronate complexes into cyclobutanes. The process involves addition of an electrophilic radical to the electron‐rich alkenyl boronate complex, leading to an α‐boryl radical. Upon one‐electron oxidation, ring‐contractive 1,2‐metalate rearrangement occurs to give a cyclobutyl boronic ester. A range of radical precursors and vinyl boronates can be employed, and chiral cyclobutanes can be accessed with high levels of stereocontrol. The process was extended to the preparation of benzo‐fused cyclobutenes and the versatility of the boronic ester was demonstrated by conversion to other functional groups.

    Research areas

  • photoredox catalysis, boron chemistry, ring contraction, metalate rearrangement, cyclobutanes

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  • Full-text PDF (author’s accepted manuscript)

    Rights statement: This is the author accepted manuscript (AAM). The final published version (version of record) is available online via Wiley at https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201915409 . Please refer to any applicable terms of use of the publisher.

    Accepted author manuscript, 1.17 MB, PDF document

    Embargo ends: 8/01/21

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    Licence: CC BY-NC

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