Ligand-Controlled Regiodivergent Palladium-Catalyzed Decarboxylative Allylation Reaction to Access α,α-Difluoroketones

被引:76
作者
Yang, Ming-Hsiu [1 ]
Orsi, Douglas L. [1 ]
Altman, Ryan A. [1 ]
机构
[1] Univ Kansas, Dept Med Chem, Lawrence, KS 66045 USA
基金
美国国家科学基金会;
关键词
allylation; fluorine; palladium; phosphine ligands; regioselectivity; MIYAURA COUPLING PROCESSES; ALLYLIC ALKYLATION; ALPHA-FLUOROKETONES; INNER-SPHERE; REGIO; AMINATION; KETONES; ESTERS; TRIFLUOROMETHYLATION; FLUOROALKYLATION;
D O I
10.1002/anie.201410039
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
alpha,alpha-Difluoroketones possess unique physicochemical properties that are useful for developing therapeutics and probes for chemical biology. To access the -allyl-,-difluoroketone substructure, complementary palladium-catalyzed decarboxylative allylation reactions were developed to provide linear and branched -allyl-,-difluoroketones. For these orthogonal processes, the fluorination pattern of the substrate enabled the ligands to dictate the regioselectivity of the transformations.
引用
收藏
页码:2361 / 2365
页数:5
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