Chinese Journal of Organic Chemistry >
Copper Mediated sp3-C—N Bond Cleavage for Synthesizing (Diarylmethyl)diarylphosphine Oxides
Received date: 2024-05-31
Revised date: 2024-09-05
Online published: 2024-09-19
Supported by
National Natural Science Foundation of China(22378106); National Natural Science Foundation of China(21706058); National Natural Science Foundation of China(21878072); National Natural Science Foundation of China(22002169); Natural Science Foundation of Hunan Province(2020JJ2011); China Postdoctoral Science Foundation(2019M662774)
Organic phosphorus compounds containing sp3-C—P(O) bonds are increasingly widely applied in catalysis, pharmaceuticals, materials, pesticides, and other fields, and their synthesis has become a research hotspot in chemistry. Diarylmethyl phosphine oxides are important organic phosphorus compounds containing sp3-C—P(O) bonds, but their synthesis is limited. Traditional methods for their synthesis require the use of halogenated compounds and harsh reaction conditions. A new method for the copper-mediated synthesis of (diarylmethyl)diarylphosphine oxides has been developed. This method involves the cleavage of the sp3-C—N bond in N-diarylmethylsulfonamides, leading to the formation of diarylmethyl carbocations. The carbocations then react with diarylphosphine oxides to construct sp3-C—P(O) bonds. Our method only requires the addition of stoichiometric, inexpensive CuBr2 and produces a series of target compounds in satisfactory yields. Thus, it provides a convenient, and cost-effective pathway for the synthesis of diarylmethyl phosphine oxides.
Jianyu Dong , Jie Huo , Ying Guo , Dan Zhou , Yongbo Zhou . Copper Mediated sp3-C—N Bond Cleavage for Synthesizing (Diarylmethyl)diarylphosphine Oxides[J]. Chinese Journal of Organic Chemistry, 2024 , 44(12) : 3713 -3719 . DOI: 10.6023/cjoc202405051
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