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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 Investigation

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

*Korea Advanced Institute of Science and Technology, Daejeon, 34141; Pohang University of Science and Technology, Pohang, 37673, Republic of Korea, Email: mbaik2805kaist.ac.kr, seunghwanpostech.ac.kr

Y. Lee, S.-y. Baek, J. Park, S.-T. Kim, S. Tussupbayev, J. Kim, M.-H. Baik, S. H. Cho, J. Am. Chem. Soc., 2017, 139, 976-984.

DOI: 10.1021/jacs.6b11757 (free Supporting Information)



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Abstract

In a transition-metal-free borylation of aryl and vinyl halides using 1,1-bis[(pinacolato)boryl]alkanes as boron source, one of the boron groups is selectively transferred in the presence of sodium tert-butoxide as the only activator. A broad range of organohalides are borylated with excellent chemoselectivity and functional group compatibility.

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Key Words

borylation


ID: J48-Y2017