Visible-Light-Mediated Deaminative Three-Component Dicarbofunctionalization of Styrenes with Benzylic Radicals

被引:157
作者
Klauck, Felix J. R. [1 ]
Yoon, Hyung [2 ]
James, Michael J. [1 ]
Lautens, Mark [2 ]
Glorius, Frank [1 ]
机构
[1] Westfalische Wilhelms Univ Munster, Organ Chem Inst, D-48149 Munster, Germany
[2] Univ Toronto, Dept Chem, Davenport Chem Labs, 80 St George St, Toronto, ON M5S 3H6, Canada
关键词
dicarbofunctionalization; deamination; redox-active; photoredox catalysis; visible-light; N-HYDROXYPHTHALIMIDE ESTERS; CARBONYL ALKYL BROMIDES; ALPHA-AMINO-ACIDS; PHOTOREDOX CATALYSIS; UNACTIVATED OLEFINS; CROSS-COUPLINGS; ONE-POT; ARYLATION; ALKENES; ARYL;
D O I
10.1021/acscatal.8b04191
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The visible-light-mediated three-component dicarbofunctionalization of styrenes using simple benzylic radicals is described. Notably, this work describes a rare example of undirected dicarbofunctionalization using unsubstituted benzyl radicals. Key to the success of this strategy was the rational design and use of benzylic pyridinium salts as radical precursors. Using this approach, abundant styrenes, electron-rich heterocycles, and benzylic amines were combined to rapidly afford a number of densely functionalized 1,1-diarylalkanes. A dipeptide-derived pyridinium salt was applied in this transformation, which resembles a visible-light-mediated deaminative generation of radicals from peptides.
引用
收藏
页码:236 / 241
页数:11
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