4.7 Article

Iron-Based Catalyst for Borylation of Unactivated Alkyl Halides without Using Highly Basic Organometallic Reagents

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 2, Pages 1948-1954

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c02364

Keywords

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Funding

  1. SERB, DST inspire faculty award [CRG/2019/002319, DST/INSPIRE/04/2015/000785]
  2. Indian Institute of Science (IISc) start-up research grant
  3. IISc Bangalore

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This study presents a new mild borylation reaction method using iron-bis amide mediated boronating agent for alkyl bromides and chlorides. The reaction shows a wide substrate scope and good functional group compatibility, with sufficient catalytic activity for primary and secondary alkyl halides. Mechanistic studies suggest that the reaction proceeds through a radical pathway.
The mild borylation of alkyl bromides and chlorides with bis(neopentylglycolato)diborane (B(2)neop(2)) mediated by iron-bis amide is described. The reaction proceeds with a broad substrate scope and good functional group compatibility. Moreover, sufficient catalytic activity was obtained for primary and secondary alkyl halides. Mechanistic studies indicate that the reaction proceeds through a radical pathway.

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