Convenient synthesis of phosphinecarboxamide and phosphinecarbothioamide by hydrophosphination of isocyanates and isothiocyanates

Masumi Itazaki; Takanari Matsutani; Tomoya Nochida; Toshiyuki Moriuchi; Hiroshi Nakazawa

doi:10.1039/C9CC08329D

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Convenient synthesis of phosphinecarboxamide and phosphinecarbothioamide by hydrophosphination of isocyanates and isothiocyanates†

Masumi Itazaki,

*^a Takanari Matsutani,^a Tomoya Nochida,^a Toshiyuki Moriuchi

^a and Hiroshi Nakazawa*^a

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* Corresponding authors

^a Department of Chemistry, Graduate School of Science, Osaka City University, Sumiyoshi-ku, Osaka 558-8585, Japan
E-mail: mitazaki@sci.osaka-cu.ac.jp, nakazawa@sci.osaka-cu.ac.jp

Abstract

Reactions of isocyanates with primary and secondary phosphines without solvent at room temperature afforded the corresponding phosphinecarboxamide (RN(H)COPR′₂) in excellent yields. This reaction system is applicable for isothiocyanates. The compounds newly obtained were fully characterized using multielement NMR spectroscopy. In addition, the molecular structure of Cl(CH₂)₂N(H)COPPh₂ was studied by single-crystal X-ray diffraction.

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DOI: https://doi.org/10.1039/C9CC08329D
Article type: Communication
Submitted: 24 Oct 2019
Accepted: 29 Nov 2019
First published: 29 Nov 2019

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Chem. Commun., 2020,56, 443-445

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Convenient synthesis of phosphinecarboxamide and phosphinecarbothioamide by hydrophosphination of isocyanates and isothiocyanates

M. Itazaki, T. Matsutani, T. Nochida, T. Moriuchi and H. Nakazawa, Chem. Commun., 2020, 56, 443 DOI: 10.1039/C9CC08329D

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Chemical Communications

Convenient synthesis of phosphinecarboxamide and phosphinecarbothioamide by hydrophosphination of isocyanates and isothiocyanates†

Abstract

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Convenient synthesis of phosphinecarboxamide and phosphinecarbothioamide by hydrophosphination of isocyanates and isothiocyanates

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