Aryl Radical Enabled, Copper-Catalyzed Sonogashira-Type Cross- Coupling of Alkynes with Alkyl Iodides

被引：0
作者：
Zeng, Xiaojun [1 ]
Wang, Chao [2 ]
Yan, Wenhao [2 ]
Rong, Jian [3 ]
Song, Yanshan [1 ]
Xiao, Zhiwei [3 ]
Cai, Aijie [2 ]
Liang, Steven H. [3 ]
Liu, Wei [2 ]
机构：
[1] Nanchang Univ, Sch Chem & Chem Engn, Nanchang 330031, Jiangxi, Peoples R China
[2] Univ Cincinnati, Dept Chem, Cincinnati, OH 45221 USA
[3] Emory Univ, Dept Radiol & Imaging Sci, Atlanta, GA 30322 USA
来源：
ACS CATALYSIS | 2023年 / 13卷 / 04期
关键词：
copper; alkyne; Sonogashira coupling; aryl radical; halogen abstraction; DECARBOXYLATIVE ALKYNYLATION; CARBOXYLIC-ACIDS; CLICK CHEMISTRY; C-C; PALLADIUM; BROMIDES; BIOMOLECULES; ACTIVATION; COMPLEXES; NICKEL;
D O I：
10.1021/acscatal.2c059012761
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：
Despite the success of Sonogashira coupling for the synthesis of arylalkynes and conjugated enynes, the engagement of unactivated alkyl halides in such reactions remains historically challenging. We report herein a strategy that merges Cu-catalyzed alkyne transfer with the aryl radical activation of carbon-halide bonds to enable a general approach for the coupling of alkyl iodides with terminal alkynes. This unprecedented Sonogashira-type cross -coupling reaction tolerates a broad range of functional groups and has been applied to the late-stage cross-coupling of densely functionalized pharmaceutical agents as well as the synthesis of positron emission tomography tracers.
引用
收藏
页码：2761 / 2770
页数：10
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