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Radical Addition to Strained σ-Bonds Enables the Stereocontrolled Synthesis of Cyclobutyl Boronic Esters

Research output: Contribution to journalArticle

Original languageEnglish
Pages (from-to)9511-9515
Number of pages5
JournalJournal of the American Chemical Society
Volume141
Issue number24
Early online date29 May 2019
DOIs
DateAccepted/In press - 29 May 2019
DateE-pub ahead of print - 29 May 2019
DatePublished (current) - 19 Jun 2019

Abstract

While radical additions to π-bonds are well established, additions to σ-bonds are far less explored. We have found that electron deficient radicals derived from alkyl iodides under visible light irradiation add to the central strained bond of bicyclobutyl (BCB)-boronate complexes and lead to 1,3-alkyl disubstituted cyclobutyl boronic esters in high yields, with full stereospecificity and high levels of stereoselectivity. Novel cyclobutyl-substituted structures, including peptide and steroid boronic ester derivatives can be accessed. Additionally, although the use of electron-rich alkyl iodides as radical precursors was found to be ineffective, an alternative route involving alkylsulfonylation of the BCB-boronate followed by reductive desulfonylation provided access to simple alkyl substituted cyclobutane products.

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  • Full-text PDF (accepted author manuscript)

    Rights statement: This is the author accepted manuscript (AAM). The final published version (version of record) is available online via ACS at https://pubs.acs.org/doi/10.1021/jacs.9b03653 . Please refer to any applicable terms of use of the publisher.

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