烷基铝试剂与亲电试剂的偶联反应研究进展

doi:10.6023/cjoc202009029

摘要/Abstract

烷基铝试剂因其反应活性高、毒性低、易于制备, 广泛应用于有机反应中. 过渡金属催化或无催化剂的条件下,有机铝试剂与亲电试剂的交叉偶联反应为多种化合物的合成提供了一种简便的方法, 并显示出比有机锂和有机镁试剂更高的官能团耐受性, 可以在硝基、酯基、羟基、氨基、腈基和内酯的存在下与羰基进行加成反应, 与亲电试剂进行偶联反应. 近年来许多有机铝试剂在交叉偶联反应中得到了较广泛的应用. 综述了近年来烷基铝试剂在交叉偶联反应中的研究成果, 涉及到各种反应体系.

关键词: 烷基铝试剂, 亲电试剂, 偶联反应, 碳碳键形成, 碳-杂原子键形成, 过渡金属, 无催化剂

Alkyl aluminum compounds are widely applied in organic reactions because of their high reactivities, low toxicities, and ease of preparation. The cross-coupling reaction of an organoalane compounds with organic electrophiles using a transition-metal catalyst or catalyst-free provides a simple method to synthesize a large variety of compounds and shows a higher functional group tolerance than organolithium and magnesium, which allows for additions to aldehydes in the presence of nitro, ester, hydroxyl, amino, nitrile and lactone moieties. Therefore, many organoalane reagents have found the most applications in cross-coupling reactions in recent years. In this paper, the recent research results about the alkylaluminum reagents applied in cross-coupling reactions are reviewed, involving various reaction systems.

Key words: alkylaluminum reagents, electrophilic reagents, cross-coupling reaction, carbon-carbon bond formation, carbon- heteroatom bond formation, transition-metal catalyst, catalyst-free

引用此文

李清寒, 罗瑞强, 吴川, 肖红柳, 郭少鹏, 张志豪, 黄哲耀, 周林. 烷基铝试剂与亲电试剂的偶联反应研究进展[J]. 有机化学, 2021, 41(4): 1489-1497.

Qinghan Li, Ruiqiang Luo, Chuan Wu, Hongliu Xiao, Shaopeng Guo, Zhihao Zhang, Zheyao Huang, Lin Zhou. Research Progress of Cross-Coupling Reactions of Alkylaluminums with Electrophiles Reagents[J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1489-1497.

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图/表 14

图1. 镍催化芳基三甲基三氟磺酸铵盐与有机铝试剂的交叉偶联反应的可能机理

Figure 1. Proposed mechanism of the cross-coupling reaction of aryltrimethylammonium triflates with organoalanes use nickel as catalyst

图式1. 镍催化氯硅烷与烷基铝试剂的交叉偶联反应

Scheme 1. Nickel catalyzed cross coupling reaction of chloro- silane with alkyl aluminides

图式2. 铜催化烯丙基卤化物与烷基铝锂的交叉偶联

Scheme 2. Copper catalyzed cross-coupling of allyl halides with alkyl aluminum lithium

图2. PN-1配体

Figure 2. PN-1 ligand

图式3. 铜催化的有机铝试剂与有机卤化物的交叉偶联

Scheme 3. Copper catalyzed cross coupling of organoalumi- nides with organohalides

图3. 可能的催化循环

Figure 3. Proposed catalytic cycle.

图4. 可能的催化循环

Figure 4. Proposed catalytic cycle

图5. 三齿膦配体

Figure 5. Tridentate phosphine ligand

图6. 2,3-二氯丁烷

Figure 6. 2,3-DCB

图7. 环状钴络合物中间体

Figure 7. A cobaltocycle intermediate

图式4. C—F键参与烷基铝的偶联反应

Scheme 4. C—F bond participates in the cross-coupling reaction of alkyl aluminum

图式5. 无催化剂条件下有机铝试剂与三氟甲基苯的偶联反应

Scheme 5. Cross-coupling reaction of organic aluminum reagent with trifluoromethylbenzene without catalyst

图式6. 羰基化合物与三烷基铝试剂直接交叉偶联的可能机理

Scheme 6. A possible mechanism of direct cross-coupling of carbonyl compounds with trialkyl aluminum reagents

图8. 异黄酮(–)等效物

Figure 8. Isoflavan (–)-equol

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