化学
薗头偶联反应
金鸡纳
对映选择合成
组合化学
配体(生物化学)
催化作用
分子
立体化学
有机化学
钯
生物化学
受体
作者
Xiaoyang Dong,Yufeng Zhang,Canliang Ma,Qiang‐Shuai Gu,Fuli Wang,Zhong‐Liang Li,Shengpeng Jiang,Xin‐Yuan Liu
出处
期刊:Nature Chemistry
[Springer Nature]
日期:2019-10-21
卷期号:11 (12): 1158-1166
被引量:234
标识
DOI:10.1038/s41557-019-0346-2
摘要
Continued development of the Sonogashira coupling has made it a well established and versatile reaction for the straightforward formation of C-C bonds, forging the carbon skeletons of broadly useful functionalized molecules. However, asymmetric Sonogashira coupling, particularly for C(sp3)-C(sp) bond formation, has remained largely unexplored. Here we demonstrate a general stereoconvergent Sonogashira C(sp3)-C(sp) cross-coupling of a broad range of terminal alkynes and racemic alkyl halides (>120 examples) that are enabled by copper-catalysed radical-involved alkynylation using a chiral cinchona alkaloid-based P,N-ligand. Industrially relevant acetylene and propyne are successfully incorporated, laying the foundation for scalable and economic synthetic applications. The potential utility of this method is demonstrated in the facile synthesis of stereoenriched bioactive or functional molecule derivatives, medicinal compounds and natural products that feature a range of chiral C(sp3)-C(sp/sp2/sp3) bonds. This work emphasizes the importance of radical species for developing enantioconvergent transformations.
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