Sulfoxides and sulfide compounds have broad-spectrum biological properties and have received considerable attention in the past few decades.Herein we reported two metal and oxidant-free,practical and efficient methods...Sulfoxides and sulfide compounds have broad-spectrum biological properties and have received considerable attention in the past few decades.Herein we reported two metal and oxidant-free,practical and efficient methods for the synthesis of highly synthetically useful and structurally diverse ortho-aminoaryl sulfoxides and 3,4,5-trisubstituted oxazolones from readily accessible N-arylhydroxylamines and N-thiophthalimides.This rapid transformation occurred smoothly to achieve chemo-and regioselective cascade rearrangements due to the differences of the protecting-groups of the nitrogen atom of N-arylhydroxyamines.DFT studies suggested that the competing S-O and S-C bond formations via SN2 nucleophilic substitution are crucial for the observed protecting-group-dependent chemoselectivity.Subsequent applications have shown that these two protocols might be powerful tools for the construction of sulfur-containing complex molecules under simple conditions.展开更多
A convenient, environmentally benign, and highly efficient protocol for the preparation of N-arylhydroxylamines from the corresponding nitroarenes in a Zn/HCOONH4/CH3CN system under ultrasound is described The advanta...A convenient, environmentally benign, and highly efficient protocol for the preparation of N-arylhydroxylamines from the corresponding nitroarenes in a Zn/HCOONH4/CH3CN system under ultrasound is described The advantages of the present method include high chemoselectivity, simple and practical work-up procedure and high yield.展开更多
基金Financial supports from the National Natural Science Foundation of China(Nos.22271176,22371171)the Taishan Scholar Project of Shandong Province(No.tsqn202306015)Shandong University were gratefully appreciated.
文摘Sulfoxides and sulfide compounds have broad-spectrum biological properties and have received considerable attention in the past few decades.Herein we reported two metal and oxidant-free,practical and efficient methods for the synthesis of highly synthetically useful and structurally diverse ortho-aminoaryl sulfoxides and 3,4,5-trisubstituted oxazolones from readily accessible N-arylhydroxylamines and N-thiophthalimides.This rapid transformation occurred smoothly to achieve chemo-and regioselective cascade rearrangements due to the differences of the protecting-groups of the nitrogen atom of N-arylhydroxyamines.DFT studies suggested that the competing S-O and S-C bond formations via SN2 nucleophilic substitution are crucial for the observed protecting-group-dependent chemoselectivity.Subsequent applications have shown that these two protocols might be powerful tools for the construction of sulfur-containing complex molecules under simple conditions.
基金Supported by the National Natural Science Foundation of China(No.20676020)the Program for Changjiang Scholars and Innovative Research Team in Universities of China(No.IRT0711).
文摘A convenient, environmentally benign, and highly efficient protocol for the preparation of N-arylhydroxylamines from the corresponding nitroarenes in a Zn/HCOONH4/CH3CN system under ultrasound is described The advantages of the present method include high chemoselectivity, simple and practical work-up procedure and high yield.
