PTABS chemistry highlighted on Organic Chemistry Portal

Bicyclic caged phosphines are unique ligand systems with properties that are unmatched compared to the normal phosphines. Limited degree of freedom coupled with steric and electronic factors that can be easily regulated, provide extra potential for the caged ligands to find applications in catalytic reactions wherein other ligands have either failed or shown lower reactivity. In literature, many such examples of caged ligands in combination with metal precursors providing enhanced reactivity than their other phosphines counterparts have been reported. Verkade with the Proazaphosphatrane ligand sytems revolutionized this field with many excellent contributions, however the application of caged ligands reduced drastically post-Verkade era until recently. The past decade has seen a major resurgence in the synthesis and application of caged ligands with research groups including ours have been able to provide convincing proof about the versatility of these ligands in the form of many state-of-the-art catalytic protocols that have found applications in academia as well as industrial processes. PTABS (Kapdiphos) developed in our research lab at ICT is now commercially available in all the leading chemical companies such as

Merck (https://lnkd.in/dbskDEWm)

Strem (https://lnkd.in/diGrTtVn)

BLDPharm (https://lnkd.in/dSWrj3Qv)

Labgle (https://lnkd.in/ditQJdNa)

Ambeed (https://lnkd.in/dYER2Svr)

Toronto Research Chemicals (https://lnkd.in/dTDZEMps) 

For more information check out our papers in this area  

1.  Parmar, U., Somvanshi, D., Kori, S., Desai, A., Dandela, R., Maity, D. K., Kapdi, A. R. Cu(II)/PTABS: Versatile Water-Soluble Recyclable Catalyst System for Pd-Free Room Temperature Amination of Chloroheteroarenes in Water. J. Org. Chem. 2021,  86, 8900-8925. 
2. Parmar, U., Kapdi, A. R. 3,5-Diaza-1-azonia-7-phosphatricyclo[3.3.1.13,7]decane, 1-(4-sulfobutyl)-, inner salt Encyclopedia of Reagents in Organic Synthesis (EROS) 2021 (first update).
3.  Shet, H., Parmar, U., Bhilare, S., Kapdi, A. R. A comprehensive review of the caged phosphines: Synthesis catalysis and future perspective.  Org. Chem. Front. 2021, 8, 1599-1656.  
4. Bhilare, S., Murthy Bandaru, S., Schulzke, C., Kapdi, A. R. 1,3,5-Triaza-7-phosphaadamantane (PTA) derived caged phosphines for palladium-catalyzed selective functionalization of nucleosides and heteroarenes. Chem. Rec. 2020 
5. Shet, H., Bhilare, S., Sanghvi, Y. S., Kapdi, A. R. Tandem homometallic and multimetallic catalysis for nucleoside modification.  Curr. Protoc. Nucleic Acid Chem. 2020, 83, e117.
6. Bhilare, S., Kori, S., Shet, H., Balaram, G., Mahendar, K., Sanghvi, Y. S., Kapdi, A. R. Scale-up of a Heck alkenylation reaction: Application to the Synthesis of an Amino-modified nucleoside “Ruth Linker” Synthesis PSP 2020
7. Ardhapure, A. A., Gayakhe, V., Bhilare, S., Kapdi, A. R., Sanghvi, Y. S., Bag, S. S., Gunturu, C. Extended fluorescent uridine analogues: Synthesis, photo-physical properties and selective interaction with BSA protein. New J. Chem. 2020, 14744-14754.
8. Bhilare, S., Shah, J., Kapdi, A. R. 3,5-Diaza-1-azonia-7-phosphatricyclo[3.3.1.13,7]decane, 1-(4-sulfobutyl)-, inner salt Encyclopedia of Reagents in Organic Synthesis (EROS) 2020. 
9. Shet, H., Bhilare, S., Sanghvi, Y. S., Kapdi, A. R.  Discovery, Synthesis, and Scale-up of Efficient Palladium Catalysts Useful for the Modification of Nucleosides and Heteroarenes Molecules 2020, 25, 1645 
10. Bhilare, S., Shah, J., Gaikwad, V., Gupta, G., Sanghvi, Y. S., Bhanage, B. M., Kapdi, A. R. Pd/PTABS: An efficient catalytic system for the aminocarbonylation of nucleosides. Synthesis 2019, 51, 4239-4248
11. Murthy Bandaru, S. S., Bhilare, S., Cardozo, J., Chrysochos, N., Schulzke, C., Sanghvi, Y. S., Gunturu, K. C., Kapdi, A. R. Pd/PTABS: Low temperature thioetherification of chloroheteroarenes. J. Org. Chem. 2019, 84, 8921-8940. 
12. Bhujbal, Y.B., Vadagaonkar, K. S., Kapdi, A. R. Pd/PTABS: Catalyst for Efficient C-H (Hetero)arylation of 1,3,4-Oxadiazoles Using Bromo(Hetero)arenes, Asian J. Org. Chem., 2019, 8, 289-295. 
13. Murthy Bandaru, S., Bhilare, S., Chryosochos, N., Gayakhe, V., Trentin. I., Schulzke, C., Kapdi, A. R.*, Pd/PTABS: Catalyst for Room Temperature Amination of Heteroarenes. Org. Lett. 2018, 20, 473-476.  
14. Bhilare, S., MuthryBandaru, S., Shah, J., Chrysochos, N., Schulzke, C., Sanghvi, Y. S., Kapdi, A. R. Pd/PTABS: Low Temperature Etherification of Chloroheteroarenes. J. Org. Chem. 2018, 83, 13088-13102. 
15. Bhilare, S., Bandaru, S., Kapdi, A. R., Sanghvi, Y. S., Schulzke, C. Pd/PTABS: An Efficient Water Soluble Catalytic System for the Amination of 6-Chloropurine Ribonucleoside and Synthesis of Alogliptin. Curr. Protoc. Nucleic Acids Chem. 2018, 74, 58. 
16. Bhilare, S., Gayakhe, V., Ardhapure, A., Sanghvi, Y. S., Schulzke, C., Borozdina, Y., Kapdi, A. R.* ‘Novel Water-Soluble Phosphatriazenes: Versatile Ligands for Suzuki-Miyaura, Sonogashira and Heck Reactions of Nucleosides’ RSC Adv. 2016, 6, 83820.