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CC BY 4.0 · Sustainability & Circularity NOW 2024; 01: a23865537
DOI: 10.1055/a-2386-5537
Original Article

NaIO4/NH2OH-mediated Efficient Synthesis of Phosphoroamidates from Anilines and Triethyl Phosphite

E. V. Venkat Shivaji Ramarao‡
1   Dr Reddy’s Institute of Life Sciences, University of Hyderabad Campus, Gachibowli, Hyderabad 500 046, India
,
Savita Gat‡
2   Department of Industrial and Engineering Chemistry, Institute of Chemical Technology, Indian Oil Odisha Campus, Samantpuri, Bhubaneswar 751013, India
,
Rana Chatterjee 
2   Department of Industrial and Engineering Chemistry, Institute of Chemical Technology, Indian Oil Odisha Campus, Samantpuri, Bhubaneswar 751013, India
,
Jayshree Solanke
2   Department of Industrial and Engineering Chemistry, Institute of Chemical Technology, Indian Oil Odisha Campus, Samantpuri, Bhubaneswar 751013, India
,
Vasudevan Dhayalan
3   Department of Chemistry, National Institute of Technology Puducherry, Karaikal 609609, Puducherry, India
,
Rambabu Dandela 
2   Department of Industrial and Engineering Chemistry, Institute of Chemical Technology, Indian Oil Odisha Campus, Samantpuri, Bhubaneswar 751013, India
› Author Affiliations Funding Information Rambabu Dandela thanks DST-SERB for Core research grants (CRG/2023/001402) and (CRG/2022/001855).
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Abstract

A simple, efficient, and metal-free method was developed for the synthesis of phosphoroamidates. In essence, a mixture of sodium periodate (NaIO4) and hydroxylamine (NH2OH⸱HCl) was used in stoichiometric amounts to execute the phosphoramidation reaction of aromatic amines and triethyl phosphites at room temperature, in open air. This method offers a practical synthesis route to afford a diverse range of phosphoroamidates via the construction of P − N bonds, with excellent functional group compatibility and good yields under mild conditions.

Keywords

Metal-free - Sodium periodate (NaIO4) - Hydroxylamine (NH2OH⸱HCl) - Available starting substrates - Phosphoroamidates - Room temperature

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2386-5537.
  • Supporting Information

Primary Data

    NO.



Publication History

Received: 10 May 2024

Accepted after revision: 12 August 2024

Accepted Manuscript online:
13 August 2024

Article published online:
09 October 2024

© 2024. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting unrestricted use, distribution, and reproduction so long as the original work is properly cited. (https://creativecommons.org/licenses/by/4.0/).

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Bibliographical Record
E. V. Venkat Shivaji Ramarao, Savita Gat, Rana Chatterjee, Jayshree Solanke, Vasudevan Dhayalan, Rambabu Dandela. NaIO4/NH2OH-mediated Efficient Synthesis of Phosphoroamidates from Anilines and Triethyl Phosphite. Sustainability & Circularity NOW 2024; 01: a23865537.
DOI: 10.1055/a-2386-5537
 

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