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Palladium-Catalyzed Benzylic Phosphorylation of Diarylmethyl Carbonates

Cite this: Org. Lett. 2018, 20, 12, 3553–3556
Publication Date (Web):May 25, 2018
https://doi.org/10.1021/acs.orglett.8b01323
Copyright © 2018 American Chemical Society
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Abstract

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A palladium-catalyzed benzylic substitution of tert-butyl diarylmethyl carbonates with a pinacol-derived H-phosphonate proceeds to deliver the corresponding benzylic phosphorylated products in good yields. Moreover, the asymmetric synthesis is possible via a Pd/(Rp,Rp)-(S)-Mandyphos-catalyzed kinetic resolution–DYKAT (dynamic kinetic asymmetric transformation) sequence, and optically active α-chiral diarylmethylphosphonates are obtained with synthetically useful yields and enantiomeric ratios (up to 50% and 92:8 er).

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The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.orglett.8b01323.

  • 1H, 13C{1H}, 19F{1H}, and 31P{1H} NMR spectra, ORTEP drawing, and NMR studies (PDF)

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CCDC 1837952 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.

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  6. Sure Siva Prasad, Dileep Kumar Singh, Ikyon Kim. One-Pot, Three-Component Approach to Diarylmethylphosphonates: A Direct Entry to Polycyclic Aromatic Systems. The Journal of Organic Chemistry 2019, 84 (10) , 6323-6336. https://doi.org/10.1021/acs.joc.9b00668
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  12. Keng Lung Lee, Joey Feld, Paul Hume, Tilo Söhnel, Erin Leitao. The Synthesis and Mechanistic Considerations of a Series of Ammonium Monosubstituted H ‐Phosphonate Salts. Chemistry – A European Journal 2021, 27 (2) , 815-824. https://doi.org/10.1002/chem.202003090
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  16. Hao Yuan, Jamal A.H. Kowah, Jun Jiang. Base-promoted hydrophosphination of para-quinone methides under ultrasonic irradiation: A rapid and efficient synthesis of diarylmethyl phosphorus oxides. Tetrahedron Letters 2020, 61 (15) , 151748. https://doi.org/10.1016/j.tetlet.2020.151748
  17. Akihiro Matsude, Koji Hirano, Masahiro Miura. Palladium‐Catalyzed Intramolecular Mizoroki‐Heck‐Type Reaction of Diarylmethyl Carbonates. Advanced Synthesis & Catalysis 2020, 362 (3) , 518-522. https://doi.org/10.1002/adsc.201901398
  18. Keng Lung Lee, Joey Feld, Yael Ben‐Tal, Zhaoyang Guo, Paul Hume, Erin M. Leitao. Facile Substituent Exchange at H ‐Phosphonate Diesters Limiting an Effective Synthesis of D ‐Phosphonate Diesters. Asian Journal of Organic Chemistry 2019, 8 (8) , 1415-1425. https://doi.org/10.1002/ajoc.201900430
  19. Jian-Quan Weng, Ling-Ling Xing, Wen-Ren Hou, Ren-Xiao Liang, Yi-Xia Jia. Palladium-catalyzed dearomative arylphosphorylation of indoles. Organic Chemistry Frontiers 2019, 6 (10) , 1577-1580. https://doi.org/10.1039/C9QO00246D
  20. Sarah M. Pound, Mary P. Watson. Asymmetric synthesis via stereospecific C–N and C–O bond activation of alkyl amine and alcohol derivatives. Chemical Communications 2018, 54 (87) , 12286-12301. https://doi.org/10.1039/C8CC07093H

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