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Photoinduced selective hydrophosphinylation of allylic compounds with diphenylphosphine oxide leading to γ-functionalized P-ligand precursors

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Abstract

A series of bifunctional phosphine compounds promising as γ-functionalized phosphine ligand precursors are conveniently synthesized by the radical addition of diphenylphosphine oxide (Ph2P(O)H) to allylic compounds under photoirradiation. The photoinduced addition proceeds regioselectively in an anti-Markovnikov manner, and phosphines having hydroxy, alkoxy, aryloxy, acyloxy, and thio groups at the γ-position can be prepared by simple operation. Interestingly, novel continuous addition of Ph2P(O)H to two molecules of allylic ethers and related compounds is also observed, although their yields are moderate. The substituent and steric effects of the allylic substituents on the radical addition are discussed in detail.

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Notes

  1. Upon treating with DIBAL-H, γ-functionalized P-ligand precursors, Ph2P(O)–CH2CH2CH2–X, (X = functional group), can be converted to the corresponding phosphines, Ph2P–CH2CH2CH2–X, which are allowed to complex with Me2S•BH3, followed by purification of thus formed Ph2P(BH3)–CH2CH2CH2–X by column chromatography. Then, deprotection using DABCO successfully affords γ-functionalized P-ligands, Ph2P–CH2CH2CH2–X.

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Acknowledgements

DPT is grateful for the support of the Ministry of Education, Culture, Sports, Science and Technology (MEXT) Scholarship Program. This research was supported by JSPS KAKENHI (B, 19H02791), (B, 19H02756), and (19K17746), from the Ministry of Education, Culture, Sports, Science and Technology, Japan, and by Kyoto-NAIST Advanced Nanotechnology Network.

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  1. Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Nakaku, Sakai, Osaka, 599-8531, Japan

    Dat Phuc Tran, Yuki Sato, Yuki Yamamoto, Shintaro Kodama, Akihiro Nomoto & Akiya Ogawa

  2. Center for Education and Research in Agricultural Innovation, Faculty of Agriculture, Saga University, 152-1 Shonan-cho, Karatsu, Saga, 847-0021, Japan

    Shin-ichi Kawaguchi

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  1. Dat Phuc Tran
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Correspondence to Shin-ichi Kawaguchi, Shintaro Kodama or Akiya Ogawa.

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Tran, D.P., Sato, Y., Yamamoto, Y. et al. Photoinduced selective hydrophosphinylation of allylic compounds with diphenylphosphine oxide leading to γ-functionalized P-ligand precursors. Res Chem Intermed 47, 3067–3078 (2021). https://doi.org/10.1007/s11164-021-04433-7

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