CC BY-ND-NC 4.0 · Synthesis 2019; 51(05): 1171-1177
DOI: 10.1055/s-0037-1610413
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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
,
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
This work was supported by Grants-in-Aid for Scientific Research (A) (no. 26248031) from JSPS and Scientific Research on Innovative Areas 2707 Middle Molecular Strategy (no. 15H05850) from MEXT.
Further Information

Publication History

Received: 12 October 2018

Accepted after revision: 26 November 2018

Publication Date:
07 January 2019 (online)


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.

Supporting Information

 
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