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Title: Regioselective copper-catalyzed oxidative coupling of α-alkylated styrenes with tertiary alkyl radicals
Authors: Wang, Cong
Liu, Rui-Hua
Tian, Ming-Qing
Hu, Xu-Hong
Loh, Teck-Peng
Keywords: Science::Chemistry
Issue Date: 2018
Source: Wang, C., Liu, R.-H., Tian, M.-Q., Hu, X.-H., & Loh, T.-P. (2018). Regioselective copper-catalyzed oxidative coupling of α-alkylated styrenes with tertiary alkyl radicals. Organic Letters, 20(13), 4032-4035. doi:10.1021/acs.orglett.8b01600
Journal: Organic Letters
Abstract: A radical-mediated oxidative cross-coupling of readily accessible α-alkylated styrenes with 1,3-dicarbonyl compounds utilizing a combination of Cu(OAc)2 and air as a catalytic system is described. Rather than requiring α-halocarbonyl compounds, this efficient approach enables direct installation of tertiary functionalized alkyl motifs to olefins with simple carbonyl derivatives. The novel protocol is characterized with high allylic selectivities via a competing β-H elimination. Both radical-clock and -trapping experiments provided clear-cut evidence for the intermediacy of an α-keto carbon-centered radical.
ISSN: 1523-7060
DOI: 10.1021/acs.orglett.8b01600
Rights: © 2018 American Chemical Society. All rights reserved.
Fulltext Permission: none
Fulltext Availability: No Fulltext
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