Synthesis, Table of Contents CC BY-ND-NC 4.0 · Synthesis 2019; 51(05): 1171-1177DOI: 10.1055/s-0037-1610413 feature Copyright with the author Bromine-Radical-Mediated Site-Selective Allylation of C(sp3)–H Bonds Mitsuhiro Ueda a Department of Chemistry, Graduate School of Science, OsakaPrefecture University, Sakai, Osaka, 599-8531, Japan , Ayami Maeda a Department of Chemistry, Graduate School of Science, OsakaPrefecture University, Sakai, Osaka, 599-8531, Japan , Kanako Hamaoka a Department of Chemistry, Graduate School of Science, OsakaPrefecture University, Sakai, Osaka, 599-8531, Japan , Mika Sasano a Department of Chemistry, Graduate School of Science, OsakaPrefecture University, Sakai, Osaka, 599-8531, Japan , Takahide Fukuyama a Department of Chemistry, Graduate School of Science, OsakaPrefecture University, Sakai, Osaka, 599-8531, Japan , Ilhyong Ryu * a Department of Chemistry, Graduate School of Science, OsakaPrefecture University, Sakai, Osaka, 599-8531, Japan b Department of Applied Chemistry, National Chiao Tung University, Hsinchu 30010, Taiwan Email: ryu@c.s.osakafu-u.ac.jp › Author Affiliations Recommend Article Abstract All articles of this category Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue Abstract The C(sp3)–H allylation of alkanes is investigated by using allyl bromides under radical reaction conditions. In many cases, methine C–H allylation preceded methylene and methyl C–H allylation with complete or a high degree of site selectivity. The C–H allylation of allylic compounds, such as allylbenzene, gives 1,5-dienes with the SH2′ reactions of the allyl radicals occurring at the less hindered carbon. Key words Key wordsC(sp3)–H allylation - bromine radicals - SH2 reaction - SH2′ reaction - site selectivity Full Text References References For reviews on site-selective C(sp3)–H functionalization, see: 1a Zhou M, Crabtree RH. Chem. Soc. Rev. 2011; 40: 1875 1b Che C.-M, Lo VK.-Y, Zhou C.-Y, Huang J.-S. Chem. Soc. Rev. 2011; 40: 1950 1c Brückl T, Baxter RD, Ishihara Y, Baran PS. Acc. Chem. Res. 2012; 45: 826 1d Liu W, Groves JT. Acc. Chem. Res. 2015; 48: 1727 1e Hartwig JF, Larsen MA. ACS. Cent. Sci. 2016; 2: 281 1f C–H Activation . In Topics in Current Chemistry . Vol. 292. Yu J.-Q, Shi Z. Springer-Verlag; Berlin: 2010 1g Milan M, Salamone M, Costas M, Bietti M. Acc. Chem. 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Chem. Int. Ed. 2012; 51: 5730 Supplementary Material Supplementary Material Supporting Information
