Photochemical Asymmetric Nickel-Catalyzed Acyl Cross-Coupling

被引:106
作者
Gandolfo, Eugenio [2 ]
Tang, Xinjun [2 ]
Roy, Sudipta Raha [2 ]
Melchiorre, Paolo [1 ,2 ]
机构
[1] ICREA, Passeig Lluis Companys 23, Barcelona 08010, Spain
[2] Barcelona Inst Sci & Technol, ICIQ Inst Chem Res Catalonia, Ave Paisos Catalans 16, Tarragona 43007, Spain
基金
欧洲研究理事会;
关键词
asymmetric catalysis; cross-coupling; nickel catalysis; photochemistry; radical chemistry; SECONDARY ALKYL ELECTROPHILES; ENANTIOSELECTIVE SYNTHESIS; SUBSTITUTION REACTIONS; NEGISHI ARYLATIONS; CARBOXYLIC-ACIDS; N-ALLYLATION; PHOTOREDOX; REAGENTS; INDOLES; ALKALOIDS;
D O I
10.1002/anie.201910168
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Photochemical enantioselective nickel-catalyzed cross-coupling reactions are difficult to implement. We report a visible-light-mediated strategy that successfully couples symmetrical anhydrides and 4-alkyl dihydropyridines (DHPs) to afford enantioenriched alpha-substituted ketones under mild conditions. The chemistry does not require exogenous photocatalysts. It is triggered by the direct excitation of DHPs, which act as a radical source and as a reductant, facilitating the turnover of the chiral catalytic nickel complex.
引用
收藏
页码:16854 / 16858
页数:5
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