Synthesis, Table of Contents Synthesis 2023; 55(11): 1744-1751DOI: 10.1055/a-1970-4584 paper Special Issue dedicated to Prof. Cristina Nevado, recipient of the 2021 Dr. Margaret Faul Women in Chemistry Award Borylation of Alkenyl Carbamates by Means of Sodium Metal Authors Shunsuke Koyama Fumiya Takahashi Hayate Saito Hideki Yorimitsu ∗ Recommend Article Abstract Buy Article(opens in new window) All articles of this category(opens in new window) Abstract Treatment of alkenyl carbamates with sodium dispersion and a co-existing boron electrophile affords alkenylboronates via the reductive cleavage of the vinylic C–O bond. The key to this borylation is an instant trapping of reactive organosodium species with the co-existing boron electrophile. Key words Key wordsalkenyl carbamate - sodium dispersion - borylation - alkenylboronate - electron transfer Full Text References References Selected reviews on transformations of C–O bonds including reactions of carbamates: 1a Rosen BM, Quasdorf KW, Wilson DA, Zhang N, Resmerita A, Garg NK, Percec V. Chem. Rev. 2011; 111: 1346 1b Li B, Yu D, Sun C, Shi Z. Chem. Eur. J. 2011; 17: 1728 1c Zeng H, Qiu Z, Domínguez-Huerta A, Hearne Z, Chen Z, Li C. ACS Catal. 2017; 7: 510 1d Qiu Z, Li C. Chem. Rev. 2020; 120: 10454 2a Kocienski P, Dixon NJ. Synlett 1989; 52 2b Sengupta S, Leite M, Raslan DS, Quesnelle C, Snieckus V. J. Org. Chem. 1992; 57: 4066 2c Madec D, Pujol S, Henryon V, Férézou JP. Synlett 1995; 435 2d Porée F, Clavel A, Betzer J, Pancrazi A, Ardisson J. Tetrahedron Lett. 2003; 44: 7553 2e Xu L, Li B, Wu Z, Lu X, Guan B, Wang B, Zhao K, Shi Z. Org. Lett. 2010; 12: 884 2f Muto K, Hatakeyama T, Yamaguchi J, Itami K. Chem. Sci. 2015; 6: 6792 2g Guo L, Hsiao C, Yue H, Liu X, Rueping M. 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Chem. 2015; 80: 6715 Supplementary Material Supplementary Material Supporting Information (PDF) (opens in new window)