Regioselective Radical Hydroboration of gem-Difluoroalkenes: Synthesis of α‑Borylated Organofluorines
A regioselective radical hydroboration of gem-difluoroalkenes was developed for the synthesis of α-difluoroalkylborons. The reaction features excellent regioselectivity, broad substrate scope, and good functional group capability. DFT calculations implicated the remarkable α-selectivity was driven f...
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Veröffentlicht in: | Organic letters 2019-10, Vol.21 (20), p.8414-8418 |
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Hauptverfasser: | , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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Zusammenfassung: | A regioselective radical hydroboration of gem-difluoroalkenes was developed for the synthesis of α-difluoroalkylborons. The reaction features excellent regioselectivity, broad substrate scope, and good functional group capability. DFT calculations implicated the remarkable α-selectivity was driven from the kinetically and thermodynamically more favorable α-addition step. The resulting α-difluoroalkylborons could be readily converted into NHC–borane-tethered monofluoroalkenes, which demonstrated unique reactivity and applicability in the synthesis of monofluoroalkene derivatives through transformations of the boron unit. |
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ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/acs.orglett.9b03173 |