Transition Metal-Free trans-Selective Alkynylboration of Alkynes

We report the first transition metal-free and trans-selective alkynylboration reaction of alkynes. This unprecedented carboboration reaction is enabled by pseudo-intramolecular activation of alkynylboronates using propargylic alcohols. The carboboration affords 4-alkynyl-1,2-oxaborol-2­(5H)-ols, whi...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2017-09, Vol.139 (36), p.12358-12361
Main Authors: Nogami, Marina, Hirano, Keiichi, Kanai, Misae, Wang, Chao, Saito, Tatsuo, Miyamoto, Kazunori, Muranaka, Atsuya, Uchiyama, Masanobu
Format: Article
Language:English
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Summary:We report the first transition metal-free and trans-selective alkynylboration reaction of alkynes. This unprecedented carboboration reaction is enabled by pseudo-intramolecular activation of alkynylboronates using propargylic alcohols. The carboboration affords 4-alkynyl-1,2-oxaborol-2­(5H)-ols, which are not only versatile building blocks but also exhibit strong violet-blue fluorescence emission.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.7b06212