Water determines the products: an unexpected Brønsted acid-catalyzed PO–R cleavage of P(iii) esters selectively producing P(O)–H and P(O)

Water determines the products: an unexpected Brønsted acid-catalyzed PO–R cleavage of P(iii) esters selectively producing P(O)–H and P(O)–R compounds

Published:2019 Issue:11 Volume:21 Page:2916-2922
ISSN:1463-9262
Container-title:Green Chemistry
language:en
Short-container-title:Green Chem.

Author:

Li Chunya¹²³⁴⁵,Wang Qi⁶⁷⁸⁹,Zhang Jian-Qiu¹²³⁴⁵,Ye Jingjing¹²³⁴⁵,Xie Ju⁶⁷⁸⁹^ORCID,Xu Qing⁶⁷⁸⁹¹⁰^ORCID,Han Li-Biao¹²³⁴⁵^ORCID

Affiliation:

1. National Institute of Advanced Industrial Science and Technology (AIST)

2. Tsukuba

3. Japan

4. Division of Chemistry

5. Faculty of Pure and Applied Sciences

6. School of Chemistry and Chemical Engineering

7. Yangzhou University

8. Yangzhou

9. China

10. College of Chemistry and Materials Engineering

Abstract

Water is unexpectedly found to determine a TfOH-catalyzed C–O cleavage reaction of trialkyl phosphites to produce H-phosphonates or alkylphosphonates selectively.

Funder

National Institute of Advanced Industrial Science and Technology

Publisher

Royal Society of Chemistry (RSC)

Subject

Pollution,Environmental Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2019/GC/C9GC01254K

Reference60 articles.

1. R. Engel , Handbook of Organophosphorus Chemistry , Marcel Dekker, Inc. , New York , 1992

2. F. R. Hartley , The Chemistry of Organophosphorus Compounds , John Wiley & Sons , Chichester , 1996 , vol. 4

3. L. D. Quin , A Guide to Organophosphorus Chemistry , Wiley-Interscience , New York , 2000

4. V. P. Kukhar and H. R.Hudson , Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activity , John Wiley & Sons , Chichester , 2000

5. J. P. Majoral , New Aspects in Phosphorus Chemistry , Springer , Berlin , vol. 1–5

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