trans-Aminoboration across Internal Alkynes Catalyzed by B(C6F5)3 for the Synthesis of Borylated Indoles

We report here a facile B­(C6F5)3 catalyzed trans-aminoboration of internal alkynes, furnishing 3-position borylated indoles at ambient temperature. This reaction proceeds with the breaking of a B–N bond and the formation of N–C and B–C bonds to produce indole and derivatives in one step. It works w...

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Bibliographic Details
Published in:Organic letters 2017-03, Vol.19 (6), p.1462-1465
Main Authors: Yuan, Kang, Wang, Suning
Format: Article
Language:English
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Summary:We report here a facile B­(C6F5)3 catalyzed trans-aminoboration of internal alkynes, furnishing 3-position borylated indoles at ambient temperature. This reaction proceeds with the breaking of a B–N bond and the formation of N–C and B–C bonds to produce indole and derivatives in one step. It works well for various boron reagents and alkynyl-anilines. The borylated indoles can be further derivatized to give column stable organoboron compounds that can be used for future functionalization.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b00437