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 Highly Cited Paper

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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
Author(s)
Yeosan Lee; Seung-yeol Baek; Jinyoung Park; Seoung-Tae Kim; Samat Tussupbayev; Jeongho Kim; Mu-Hyun Baik; Seung Hwan Cho
Publication Date
2017-01
Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.139, no.2, pp.976 - 984
Publisher
AMER CHEMICAL SOC
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
URI
https://pr.ibs.re.kr/handle/8788114/3958
ISSN
0002-7863
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
Files in This Item:
112-SHC-MFreeBorylation (1).pdfDownload

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