Palladium Catalyzed Carbonylative Coupling of Alkyl Boron Reagents with Bromodifluoroacetamides

被引：30
|
作者：
Yin, Hongfei [1 ,2 ]
Kumke, Jakob J. [1 ,2 ]
Domino, Katrine [1 ,2 ]
Skrydstrup, Troels [1 ,2 ]
机构：
[1] Aarhus Univ, Interdisciplinary Nanosci Ctr iNANO, Carbon Dioxide Activat Ctr CADIAC, Gustav Wieds Vej 14, DK-8000 Aarhus C, Denmark
[2] Aarhus Univ, Dept Chem, Gustav Wieds Vej 14, DK-8000 Aarhus C, Denmark
来源：
ACS CATALYSIS | 2018年 / 8卷 / 05期
基金：
新加坡国家研究基金会;
关键词：
palladium catalysis; carbonylative Suzuki; alkyl substrates; carbon-13; isotope-labeling; fluoride; CROSS-COUPLINGS; ALPHA-ARYLATION; SUZUKI REACTIONS; ARYL; BROMIDES; FLUORINE; DIFLUOROALKYLATION; CHLORIDES; ACIDS; ALPHA; ALPHA-DIFLUOROKETONES;
D O I：
10.1021/acscatal.8b00420
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：
A catalytic protocol for the preparation of alpha,alpha-difluoro-beta-alkyl-beta-ketoamides is developed employing a Pd-mediated carbonylative Suzuki coupling between alkylboron reagents and bromodifluoroacetamides with COgen as the CO source. The reaction reveals good functional group tolerance providing a broad selection of alpha,alpha-difluoro-beta-alkyl-beta-ketoamides in moderate to good yields, which represent useful precursors for further synthetic manipulation. Finally, the methodology is amenable to C-13-isotope labeling at the ketone carbon applying C-13-COgen.
引用
收藏
页码：3853 / +
页数：11
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