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Diboronic Acid Usable for the Direct Synthesis of Aromatic Boric Acid Derivatives
Tetrahydroxydiborane (1) is a useful boric acids group-introducing reagent and is used for the synthesis of aromatic boric acid derivatives.1-5) For instance, 1 successfully reacts with aryl chlorides under the conditions of Palladium-XPhos ligands-catalytic systems to afford the desired aryl boric acids. After the borylations, their diesters or trifluoroborates are further obtained by the esterification with some diols or the treatment with KHF2 respectively.1-3) For other catalytic systems to perform this reaction, nickel-catalyzed aryl borylations have been developed.4) Recently, transition-metal-free aryl borylations have been reported. This easy aryl borylation proceeds via the aryl diazonium salt intermediates formed from aromatic amines.5)
References
- 1)G. A. Molander, S. L. J. Trice, S. D. Dreher, J. Am. Chem. Soc. 2010, 132, 17701.
- 2)G. A. Molander, S. L. J. Trice, S. M. Kennedy, S. D. Dreher, M. T. Tudge, J. Am. Chem. Soc. 2012, 134, 11667.
- 3)G. A. Molander, S. L. J. Trice, S. M. Kennedy, J. Org. Chem. 2012, 77, 8678.
- 4)G. A. Molander, L. N. Cavalcanti, C. García-García, J. Org. Chem. 2013, 78, 6427.
- 5)W. Erb, A. Hellal, M. Albini, J. Rouden, J. Blanchet, Chem. Eur. J. 2014, 20, 6608.