Green hydroboration of carboxylic acids and mechanism investigation
1Department of Chemistry and Materials Science, College of Science, Nanjing Forestry University, Nanjing 210037, China. mengtao@njfu.edu.cn xuliqby@njfu.edu.cn.
Abstract:
A catalyst-free and solvent-free method for the hydroboration of a variety of carboxylic acids with pinacolborane was developed. The hydroboration of various aromatic and aliphatic carboxylic acids as well as dicarboxylic acids with HBpin could be completed within 6 h at room temperature or within 1 h at 60 °C to give the products in quantitative yields under neat conditions without the need for any solvent or metal catalyst. The possible reaction mechanism was investigated in detail based on the corresponding DFT calculations and the stoichiometric reaction of acetic acid with different equivalents of HBpin (at room temperature and 0 °C) and it revealed the stepwise nature of the protocol.
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