镍催化醇衍生物构筑碳-碳键的偶联反应研究进展
收稿日期: 2021-06-10
修回日期: 2021-06-22
网络出版日期: 2021-07-20
基金资助
上海市“超级博士后”激励计划(2020272); 国家自然科学基金(21620102003); 国家自然科学基金(21772119); 国家自然科学基金(21831005)
Development of Nickel-Catalyzed Cross-Coupling of Alcohol Derivatives to Construct Carbon-Carbon Bonds
Received date: 2021-06-10
Revised date: 2021-06-22
Online published: 2021-07-20
Supported by
Shanghai Post-Doctoral Excellence Program(2020272); National Natural Science Foundation of China(21620102003); National Natural Science Foundation of China(21772119); National Natural Science Foundation of China(21831005)
过渡金属催化构筑碳-碳键的交叉偶联反应由于其高效性、高选择性而得到了研究人员的广泛关注. 近年来, 含C(sp3)—O键的亲电试剂由于其商业易得或容易合成、反应选择性高、环境友好等优点而被用来替代有机卤化物, 应用到构建C(sp3)—C键的交叉偶联反应中. 一系列高效催化体系得以陆续报道, 其中镍催化剂由于其储量丰富、价格便宜以及独特的催化活性和选择性而被逐步应用到此类反应中, 并取得了显著的成果. 综述了镍催化醇衍生物参与的偶联反应的最新研究进展, 主要包括镍催化甲醇或伯醇衍生物参与的偶联反应, 镍催化仲醇衍生物参与的偶联反应, 镍催化叔醇衍生物参与的偶联反应, 以及镍催化缩醛和N,O-缩醛衍生物参与的偶联反应等.
吴良 , 魏瀚林 , 陈建中 , 张万斌 . 镍催化醇衍生物构筑碳-碳键的偶联反应研究进展[J]. 有机化学, 2021 , 41(11) : 4208 -4239 . DOI: 10.6023/cjoc202106021
Transition metal-catalyzed cross-coupling reactions for building carbon-carbon bonds have received extensive attention due to their high efficiency and selectivity. In recent years, electrophiles which containing C(sp3)—O bonds have been used to replace organic halides in cross-coupling reactions for the construction of C(sp3)—C bonds, due to their advantages of commercial availability or facile synthesis, high reaction selectivity, and environmental friendliness. Among those reported highly efficient catalysts, nickel catalysts have been gradually applied to such reactions and achieved remarkable advances due to their earth-abundant, cheap, unique catalytic activities and selectivity. Because of the small radius of the nickel atom, C(sp3)—Ni can inhibit and/or manipulate β-H elimination reactions, which reduces the formation of by-products. Nickel has several variable valence states and can flexibly participate in redox-neutral coupling reactions and reductive cross-coupling reactions. The latest research progress in nickel-catalyzed coupling reactions employing alcohol derivatives as electrophiles is reviewed. It is separated into four sections including nickel-catalyzed cross-coupling reactions involving methanol or primary alcohol derivatives, nickel-catalyzed cross-coupling reactions involving secondary alcohol derivatives, nickel-catalyzed cross-coupling reactions involving acetal and N,O-acetal derivatives, and nickel-catalyzed cross-coupling reactions involving tertiary alcohol derivatives.
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