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Facile Synthesis of α-Boryl-Substituted Allylboronate Esters Using Stable Bis[(pinacolato)boryl]methylzinc Reagents

Minkyeong Shin, Minjae Kim, Chiwon Hwang, Hyojae Lee, Hyunchul Kwon, Jinyoung Park, Eunsung Lee and Seung Hwan Cho*

*Department of Chemistry, Pohang University of Science and Technology (POSTECH), Pohang 37673, Rep. of Korea, Email: seunghwanpostech.ac.kr

M. Shin, M. Kim, C. Hwang, H. Lee, H. Kwon, J. Park, E. Lee, S. H. Cho, Org. Lett., 2020, 22, 2476-2480.

DOI: 10.1021/acs.orglett.0c00721



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Abstract

Bis[(pinacolato)boryl]methylzinc halides are solid storable reagents that can be used in copper-catalyzed coupling reactions with vinyliodonium salts under mild conditions. The reaction shows broad scope with respect to vinyliodonium salts, affording various α-boryl-substituted allylboronate esters in good yields. Synthetic applications of the obtained products are also demonstrated.

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Key Words

allylboronates, iodonium salts


ID: J54-Y2020