PTABS: A Unique Water-Soluble π-Acceptor Caged Phosphine

Rajesh Sahu; Anant R. Kapdi

doi:10.1055/a-1988-1861

Synlett, Table of Contents

Synlett 2023; 34(08): 912-930
DOI: 10.1055/a-1988-1861

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PTABS: A Unique Water-Soluble π-Acceptor Caged Phosphine

Authors

Rajesh Sahu
Anant R. Kapdi ∗

Abstract

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The authors would like to dedicate this account to Prof. Ian J. S. Fairlamb.

Abstract

Caged phosphines have unique structures and provide many advantageous properties that can be fine-tuned to develop efficient catalytic systems. Our research group recently introduced a highly water-soluble caged phosphine: PTABS (KapdiPhos), which is a derivatized form of triazaphosphaadamantane, and explored its applicability as a strongly π-accepting ligand in combination with metals such as Pd or Cu in a variety of cross-coupling reactions of biologically relevant halonucleosides as well as chloroheteroarenes. This account details our journey from ideation to the various catalytic applications of the ligands and eventually to its commercialization.

1 Introduction

2 Derivatization of PTA to PTABS and Its Applications

2.1 Nucleoside Modification

2.2 Heteroarene Modification

3 Conclusion

4 Summary and Future Outlook

Key words

caged phosphines - triazaphosphaadamantane - cross-coupling - palladium catalysis - nucleosides - heteroarenes - active pharmaceutical ingredients

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References

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