New Strategies for Activation of Phosphonates/Phosphates to Forge Functional Phosphorus Compounds

Hai Huang; Jun Yong Kang

doi:10.1055/s-0037-1611699

Synlett, Table of Contents

Synlett 2019; 30(06): 635-641
DOI: 10.1055/s-0037-1611699

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New Strategies for Activation of Phosphonates/Phosphates to Forge Functional Phosphorus Compounds

Hai Huang

^aDepartment of Chemistry and Biochemistry, University of Nevada Las Vegas, 4505 S. Maryland Parkway, Las Vegas, Nevada, 89154-4003, USA Email: junyong.kang@unlv.edu

^bDepartment of Applied Chemistry, College of Chemistry and Molecular Engineering, Nanjing Tech University, No. 30 Puzhu Road (S), Nanjing 211816, P. R. of China

,

Jun Yong Kang *

^aDepartment of Chemistry and Biochemistry, University of Nevada Las Vegas, 4505 S. Maryland Parkway, Las Vegas, Nevada, 89154-4003, USA Email: junyong.kang@unlv.edu

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Abstract

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Abstract

Organophosphonate analogues are important structural motifs that are present in bioactive natural products, pharmaceuticals, and agrochemicals. Because they are useful in a broad range of applications, much effort has focused on developing efficient synthetic methods that enable access to organophosphonates and their derivatives. However, currently available synthetic procedures rely on harsh reaction conditions and are limited to a narrow substrate scope. Our lab has recently made important advances in leveraging inert phosphonates/phosphates into functional phosphorus compounds such as mixed phosphonates, phosphates, and mixed aryl phosphate derivatives. Presented herein is an overview of recent achievements in the synthesis of phosphonate/phosphate derivatives and a summary of our recent accomplishments in Tf₂O-promoted activating strategy of phosphonate analogues.

1 Introduction

2 Direct Activating Strategy of Phosphonate Analogues

3 Late-stage Phosphonylation of Natural Compounds

4 Potential Applications

5 Summary

Key words

phosphorylation - phosphonate - phosphate - phosphinate - mixed phosphonate - mixed phosphate - triflic anhydride

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References

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