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ۼ : 17-01-02 09:42
[2017.01]ȯ 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 Invesitigation
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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 Invesitigation

 

Yeosan Lee, Seung-yeol Baek, Jinyoung Park, Seoung-Tae Kim, Samat Tussupbayev, Jeongho Kim, Mu-Hyun Baik*, Seung Hwan Cho*




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 -borylcarbanion, generated in-situ from the reaction of 1,1-bis[(pinacolato)boryl]alkanes with an alkoxide base, facilitate the borylation reactions.




ҷ ȭչ 1,1-ų̺ؼ ȭչ ؼȭ Ͽ Ƹؼ ȭչ ռ ִ ο Ͽ. ߵ ݼ ʰ ҷ ȭչ ؼȭ Ű ġ پ ü Ȯ Ͽ.  ο ظ 돞 ɵ ִ ̷ Ŀ Ͽ, Ƹ ̿ ߰ü Ȯ Ͽ. 1 ̿ л ȭ Ⱓ ̸,  ȭ о ְ ϳ Journal of the American Chemical Society (JACS) 2017 1 Ȯ Ǿ.



 
 

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