A strategy for the transition-metal-free C(sp2)−C(sp3) cross-coupling of α-(pseudo)halo aliphatic ketones and arylboronic acids via a 1,4-metallate shift is demonstrated. The reaction proceeds under mild conditions in the presence of base, and offers an operationally simple method for the construction of C(sp2)−C(sp3) bonds.
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References
Miyaura, N. & Suzuki, A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem. Rev. 95, 2457–2483 (1995). A review article that presents Suzuki cross-coupling.
Kambe, N., Iwasaki, T. & Terao, J. Pd-catalyzed cross-coupling reactions of alkyl halides. Chem. Soc. Rev. 40, 4937–4947 (2011). A review article that presents the difficulties and progress of palladium-promoted coupling reactions involving C(sp3)–X bonds.
Yang, K. & Song, Q. Tetracoordinate boron intermediates enable unconventional transformations. Acc. Chem. Res. 54, 2298–2312 (2021). A review article that presents our research on the chemistry of tetracoordinate boron intermediates.
Yang, K. et al. Passerini-type reaction of boronic acids enables α-hydroxyketones synthesis. Nat. Commun. 12, 441 (2021). This paper reports several 1,4-metallate migrations of tetracoordinate boron intermediates.
He, Z., Song, F., Sun, H. & Huang, Y. Transition-metal-free Suzuki-type cross-coupling reaction of benzyl halides and boronic acids via 1,2-metalate shift. J. Am. Chem. Soc. 140, 2693–2699 (2018). This paper explains the migration ability of different boronic acids.
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This is a summary of: Li, X. et al. Transition-metal-free C(sp2)–C(sp3) cross-coupling of α-(pseudo)halo aliphatic ketones with boronic acids via a 1,4-metallate shift. Nat. Synth. https://doi.org/10.1038/s44160-023-00373-9 (2023).
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Synthesis of α-aryl ketones through transition-metal-free cross-coupling. Nat. Synth 2, 1138–1139 (2023). https://doi.org/10.1038/s44160-023-00374-8
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DOI: https://doi.org/10.1038/s44160-023-00374-8