Research Progress of Cross-Coupling Reactions of Alkylaluminums with Electrophiles Reagents

doi:10.6023/cjoc202009029

Abstract

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

Cite this article

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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Fig. & Tab. 14

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

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

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

Figure 2. PN-1 ligand

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

Figure 3. Proposed catalytic cycle.

Figure 4. Proposed catalytic cycle

Figure 5. Tridentate phosphine ligand

Figure 6. 2,3-DCB

Figure 7. A cobaltocycle intermediate

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

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

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

Figure 8. Isoflavan (–)-equol

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