镍
催化作用
烷基
芳基
卤化物
试剂
光化学
第2组金属有机化学
偶联反应
过渡金属
碳纤维
组合化学
材料科学
分子
立体化学
化学
有机化学
复合材料
复合数
作者
Yadong Gao,Chao Yang,Songlin Bai,Xiaolei Liu,Qingcui Wu,Jing Wang,Chao Jiang,Xiangbing Qi
出处
期刊:Chem
[Elsevier]
日期:2020-03-01
卷期号:6 (3): 675-688
被引量:59
标识
DOI:10.1016/j.chempr.2019.12.010
摘要
Transition-metal-catalyzed cross-coupling reactions between naturally abundant sp3-hybridized carbon centers facilitate access to diverse molecules with complex three-dimensional structures. Organometallic compounds are among one of the most powerful reagents that are broadly used in carbon–carbon bond formations. Although sp2-hybridized organometallic compounds are widely employed in cross-couplings, sp3-hybridized organometallic coupling partners are less developed. Herein, we report visible-light-induced single nickel-catalyzed C(sp3)–C(sp3), C(sp3)–C(sp2), and C(sp3)–C(sp) cross-coupling reactions using alkylzirconocenes, which are easily generated in situ from terminal or internal unactivated alkenes through hydrozirconation and chain walking. This method is mild and applicable for a large range of substrates including primary, secondary, tertiary alkyl, aryl, alkenyl, alkynyl halides, and a variety of alkenes. Mechanistic studies suggest a novel nickel-catalyzed radical cross-coupling pathway, which represents the first visible-light-induced transformation of alkylzirconocenes.
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