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

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

Publication History

Received: 20 November 2022

Accepted after revision: 27 November 2022

Accepted Manuscript online:
27 November 2022

Article published online:
03 January 2023

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