ortho-Selective C−H Alkenylation of Pyridines Enabled by a Heterometallic Mg−Ni−Mg Complex
Haoyu Wen1,2, Yanping Cai1,2(蔡艳苹)*, Xin Xu1,2(徐信)*
1State Key Laboratory of Bioinspired Interfacial Materials Science, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. China
2Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. China
Org. Lett., 2026,28, 5350–5355
Abstract: This work reports the ortho-selective C–H alkenylation of diverse pyridines with alkynes catalyzed by the heterometallic Mg–Ni–Mg complex [(LMg)2Ni(C2H4)2] {L = [(DippNCMe)2CH]− and Dipp = 2,6-iPr2C6H3}. This protocol delivers a wide range of C2-alkenylpyridines with high regio- and stereoselectivities (>19:1 rr and >19:1 E/Z). The stoichiometric reaction of [(LMg)2Ni(C2H4)2] with 4-methylpyridine led to the isolation and structural characterization of a key C–H metalation intermediate, which provides direct evidence for a Mg–Ni cooperative ortho C–H activation process.
Article information: https://doi.org/10.1021/acs.orglett.6c00739