ARTICLE

Copper Mediated sp3-C—N Bond Cleavage for Synthesizing (Diarylmethyl)diarylphosphine Oxides

  • Jianyu Dong ,
  • Jie Huo ,
  • Ying Guo ,
  • Dan Zhou ,
  • Yongbo Zhou
Expand
  • a School of Physics and Chemistry, Hunan First Normal University, Changsha 410205
    b Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082
†The authors contributed equally to this work.
*Corresponding authors. E-mail:;

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)

Abstract

Organic phosphorus compounds containing sp3-CP(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-CP(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-CN bond in N-diarylmethylsulfonamides, leading to the formation of diarylmethyl carbocations. The carbocations then react with diarylphosphine oxides to construct sp3-CP(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.

Cite this article

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

References

[1]
(a) Baslé O.; Li C. J. Chem. Commun. 2009, 4124.
[1]
(b) Yang J.; Xiao J.; Zhou Y.; Chen T.; Yin S.; Han L. Chin. J. Org. Chem. 2017, 37, 1055 (in Chinese).
[1]
(杨佳, 肖晶, 周永波, 陈铁桥, 尹双凤, 韩立彪, 有机化学, 2017, 37, 1055.)
[1]
(c) Mo J. N.; Sun S.; Xu H.; Shu H.; Zhao J. Org. Lett. 2024, 26, 2197.
[1]
(d) Hirota E.; Hirashima S. I.; Morita R.; Takase J.; Matsushima Y.; Nakashima K.; Akutsu H.; Miura T. Org. Lett. 2024, 26, 1797.
[1]
(e) Xiong B.; Shi C.; Ren Y.; Xu W.; Liu Y.; Zhu L.; Cao F.; Tang K. W.; Yin S. F. J. Org. Chem. 2024, 89, 3033.
[1]
(f) Cheng Y.; Zhen J.; Chai L.; Wang J.; Yin J.; Zhu L.; Li C. Angew. Chem. Int. Ed. 2024, 63, e202316764.
[1]
(g) Yin Y.; Yang J.; Yan K.; Zeng T.; Lin H.; Ling J.; Wang S.; Wen J. Green Chem. 2024, 26, 832.
[2]
(a) Chen Q.; Wang X.; Yu G.; Wen C.; Huo Y. Org. Chem. Front. 2018, 5, 2652.
[2]
(b) Lv Y.; Xie J.; Pu W.; Wang X.; Zhang H.; Li X.; Liu Y.; Chen F.; Xu Y. Adv. Synth. Catal. 2023, 365, 4170.
[2]
(c) Liu L.; Liu M.; Liu B.; Wang Q.; Li Y.; Feng K.; Qiu R.; Zhou Y. Tetrahedron Lett. 2023, 133, 154823.
[2]
(d) Chen L.; Zhou Z.; Zhang S.; Li X.; Ma X.; Dong J. Chem. Commun. 2019, 55, 13693.
[3]
(a) Huang W. B.; Qiu L. Q.; Ren F. Y.; He L. N. Chem. Commun. 2021, 57, 9578.
[3]
(b) Reich D.; Noble A.; Aggarwal V. K. Angew. Chem. Int. Ed. 2022, 61, e202207063.
[3]
(c) Wang Y.; Wu X.; Yang L.; Liu W.; Zhang Z.; Xie X. Org. Biomol. Chem. 2023, 21, 2955.
[3]
(d) Backx S.; Dejaegere A.; Simoens A.; Van de Poel J.; Krasowska D.; Stevens C. V.; Mangelinckx S. Eur. J. Org. Chem. 2023, 26, e202300172.
[3]
(e) Ma C.; Li X.; Chen X.; He X.; Zhang S. T.; Jiang Y. Q.; Yu B. Org. Lett. 2023, 25, 8016.
[3]
(f) Guo Y.; Li N.; Li J.; Bi X.; Gao Z.; Duan Y. N.; Xiao J. Commun. Chem. 2023, 6, https://doi.org/10.1038/s42004-023-00826-4.
[4]
Yadav A.; Kumar D.; Mishra M. K.; Deeksha; Tripathi C. B. J. Org. Chem. 2021, 86, 2000.
[5]
(a) Hicks I.; McTague J.; Hapatsha T.; Teriak R.; Kaur P. Molecules 2020, 25, 290.
[5]
(b) Shen K.; Feng C.; Liu Y.; Yi D.; Lin P.; Li H.; Gong Y.; Wei S.; Fu Q.; Zhang Z. Org. Biomol. Chem. 2023, 21, 9341
[6]
(a) Barney R. J.; Richardson R. M.; Wiemer D. F. J. Org. Chem. 2011, 76, 2875.
[6]
(b) Liu C.; Szostak M. Angew. Chem. Int. Ed. 2017, 56, 12718.
[6]
(c) Wen J.; Sun X.; Yan K.; Yan T.; Liu Z.; Li Y.; Yang J. Org. Chem. Front. 2024, 11, 796.
[6]
(d) Lei Z.; Zhang W.; Wu J. ACS Catal. 2023, 13, 16105.
[6]
(e) Li C. K.; Tao Z. K.; Shoberu A.; Zhang W.; Zou J. P. Org. Lett. 2022, 24, 6083.
[7]
(a) Zhang B.; Liu L.; Mao S.; Zhou M.; Wang H.; Li L. Eur. J. Org. Chem. 2019, 2019, 3898.
[7]
(b) Zhou X.; Wang J.; Shen Y.; Ma D.; Zhao Y.; Wu J. J. Org. Chem. 2023, 88, 17521.
[7]
(c) Zhang C.; Li Z.; Zhu L.; Yu L.; Wang Z.; Li C. J. Am. Chem. Soc. 2013, 135, 14082.
[7]
(d) Ahmed S.; Shafeeq Z.; Hussain F.; Ahmed Q. N. Chem. Commun. 2023, 59, 12334.
[7]
(e) Wang L. L.; Zhou H.; Cao Y. X.; Zhang C.; Ren Y. Q.; Li Z. L.; Gu Q. S.; Liu X. Y. Nat. Synth. 2023, 2, 430.
[8]
Aher Y. N.; Pawar A. B. Org. Biomol. Chem. 2019, 17, 7536.
[9]
(a) Niu M.; Fu H.; Jiang Y.; Zhao Y. Chem. Commun. 2007, 272.
[9]
(b) Rajeshwaran G. G.; Nandakumar M.; Sureshbabu R.; Mohanakrishnan A. K. Org. Lett. 2011, 13, 1270.
[10]
Pallikonda G.; Chakravarty M. Eur. J. Org. Chem. 2012, 2013, 944.
[11]
Lee K.-Y.; Lee H.-S.; Kim H.-S.; Kim J.-N. Bull. Korean Chem. Soc. 2008, 29, 1441.
[12]
Liu C.; Li M.; Yang C.; Tian S. Chem. Eur. J. 2008, 15, 793.
[13]
Liu C. R.; Yang F. L.; Jin Y. Z.; Ma X. T.; Cheng D. J.; Li N.; Tian S. K. Org. Lett. 2010, 12, 3832.
[14]
Yang C. F.; Wang J. Y.; Tian S. K. Chem. Commun. 2011, 47, 8343.
[15]
Liu C. R.; Wang T. T.; Qi Q. B.; Tian S. K. Chem. Commun. 2012, 48, 10913.
[16]
Hu C.; Hong G.; Qian X.; Kim K. R.; Zhu X.; Wang L. Org. Biomol. Chem. 2017, 15, 4984.
[17]
Dong J.; Liu L.; Ji X.; Shang Q.; Liu L.; Su L.; Chen B.; Kan R.; Zhou Y.; Yin S. F.; Han L. B. Org. Lett. 2019, 21, 3198.
[18]
Zhu M.; Liu J.; Yu J.; Chen L.; Zhang C.; Wang L. Org. Lett. 2014, 16, 1856.
[19]
Montel S.; Jia T.; Walsh P. J. Org. Lett. 2013, 16, 130.
[20]
Zhuang H.; Wan P.; Miao C.; Yang Y.; Liang S.; Han F. J. Org. Chem. 2024, 89, 2397.
Outlines

/