Copper-catalyzed regioselective C-H sulfonyloxylation of electron-rich arenes with p-toluenesulfonic acid has been developed. Electron-rich benzene derivatives and heteroarenes can undergo this C-H sulfonyloxylation reaction to generate aryl tosylates. Furthermore, sulfonyloxylation of aryl(mesityl)iodonium sulfonates has also been investigated. Both aryl(mesityl)iodonium tosylates and triflates can react smoothly to get aryl sulfonates. The formed aryl sulfonates can be converted to phenols, as well as used as good partners of cross-coupling reactions.

The density function B3LYP method has been used to optimize the geometries of the luteolin, thymine and luteolin‐thymine complexes at 6‐31+G∗︁ basis. The vibrational frequencies have been studied at the same level to analyze these seventeen complexes, respectively. Theories of atoms in molecules (AIM) and natural bond orbital (NBO) have been utilized to investigate the hydrogen bonds involved in all the systems. The interaction energies of the complexes corrected by basis set superposition error are between −93.00–−76.69 kJ/mol. The calculating results indicate that strong hydrogen bonding interactions have been found in the luteolin‐thymine complexes.

The interacting patterns and mechanism of the catechin and cytosine have been investigated using the density functional theory B3LYP method with 6-31+G* basis set. Eleven stable structures of the catechin-cytosine complexes have been found respectively. The results indicate that the complexes are mainly stabilized by the hydrogen bonding interactions. Theories of atoms in molecules (AIM) and natural bond orbital (NBO) have been utilized to investigate the hydrogen bonds involved in all the systems. The interaction energies of all the complexes which were corrected for basis set superposition error (BSSE), are from 17.35 to 43.27 kJ/mol. The results show that the hydrogen bonding contributes to the interaction energies dominantly. The corresponding bonds stretching motions in all the complexes are red-shifted relative to that of the monomer, which is in good agreement with experimental results. catechin, cytosine, DNA bases, density functional theory, hydrogen bond

The interacting patterns and mechanism of the catechin and guanine have been investigated with the density functional theory B3LYP method by 6-31G* basis set. Fourteen stable structures for the catechin-guanine complexes have been found which form two hydrogen bonds at least. The results indicate that the complexes are mainly stabilized by the hydrogen bonding interactions. At the same time, the number and strength of hydrogen bond play a co-determinant parts in the stability of the complexes which can form two or more hydrogen bonds. Theories of atoms in molecules (AIM) and natural bond orbital (NBO) have been adopted to investigate the hydrogen bonds involved in all systems. The interaction energies of all complexes have been corrected for basis set superposition error (BSSE), ranging from -38.86 to -14.56 kJ/mol. The results showed that the hydrogen bonding contributes to the interaction energies dominantly. The corresponding bonds stretching motions in all complexes are red-shifted relative to that of the monomer, which is in agreement with experimental results.

The interacting patterns and mechanism of the catechin and thymine have been investigated with the density functional theory Becke's three-parameter nonlocal exchange functional and the Lee, Yang, and Parr nonlocal correlation functional (B3LYP) method by 6−31+G* basis set. Thirteen stable structures for the catechin-thymine complexes have been found which form two hydrogen bonds at least. The vibrational frequencies are also studied at the same level to analyze these complexes. The results indicated that catechin interacted with thymine by three different hydrogen bonds as N—H···O, C—H···O, O—H···O and the complexes are mainly stabilized by the hydrogen bonding interactions. Theories of atoms in molecules and natural bond orbital have been adopted to investigate the hydrogen bonds involved in all systems. The interaction energies of all complexes have been corrected for basis set superposition error, which are from −18.15 kJ/mol to −32.99 kJ/mol. The results showed that the hydrogen bonding contribute to the interaction energies dominantly. The corresponding bonds stretching motions in all complexes are red-shifted relative to that of the monomer, which is in agreement with experimental results.