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CC BY-ND-NC 4.0 · Synthesis 2019; 51(05): 1171-1177
DOI: 10.1055/s-0037-1610413
DOI: 10.1055/s-0037-1610413
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Bromine-Radical-Mediated Site-Selective Allylation of C(sp3)–H Bonds
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.Weitere Informationen
Publikationsverlauf
Received: 12. Oktober 2018
Accepted after revision: 26. November 2018
Publikationsdatum:
07. Januar 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
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610413.
- Supporting Information
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For reviews on site-selective C(sp3)–H functionalization, see:
For selected recent papers on site-selective C(sp3)–H functionalization, see:
For site-selective radical C–H bromination, see:
For radical allylations of alkane C(sp3)–H bonds, see:
For radical allylations of benzylic C(sp3)–H bonds and α-C(sp3)–H bonds of heteroatoms (N, O), see: