Chemoselective Coupling of 1,1-Bis[(pinacolato)boryl]alkanes for the Transition-Metal-Free Borylation of Aryl and Vinyl Halides: A Combined Experimental and Theoretical Investigation
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Title
- Chemoselective Coupling of 1,1-Bis[(pinacolato)boryl]alkanes for the Transition-Metal-Free Borylation of Aryl and Vinyl Halides: A Combined Experimental and Theoretical Investigation
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Author(s)
- Yeosan Lee; Seung-yeol Baek; Jinyoung Park; Seoung-Tae Kim; Samat Tussupbayev; Jeongho Kim; Mu-Hyun Baik; Seung Hwan Cho
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Publication Date
- 2017-01
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Journal
- JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.139, no.2, pp.976 - 984
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Publisher
- AMER CHEMICAL SOC
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Abstract
- A new transition-metal-free borylation of aryl and vinyl halides using 1,1-bis[(pinacolato)boryl]alkanes as boron sources is described. In this transformation one of the boron groups from 1,1-bis[(pinacolato)boryl]alkanes is selectively transferred to aryl and vinyl halides in the presence of sodium tert-butoxide as the only activator to form organoboronate esters. Under the developed borylation conditions, a broad range of organohalides are borylated with excellent chemoselectivity and functional group compatibility, thus offering a rare example of a transition-metal-free borylation protocol. Experimental and theoretical studies have been performed to elucidate the reaction mechanism, revealing the unusual formation of Lewis acid/base adduct between organohalides and α-borylcarbanion, generated in situ from the reaction of 1,1-bis[(pinacolato)boryl]alkanes with an alkoxide base, to facilitate the borylation reactions. © 2016 American Chemical Society
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URI
- https://pr.ibs.re.kr/handle/8788114/3958
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DOI
- 10.1021/jacs.6b11757
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ISSN
- 0002-7863
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Appears in Collections:
- Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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