Silica-Supported Oligomeric Benzyl Phosphate (Si-OBP) and Triazole Phosphate (Si-OTP) Alkylating Reagents

Maity, Pradip K.; Faisal, Saqib; Rolfe, Alan; Stoianova, Diana; Hanson, Paul R.

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Issue Date

2015-10-16

Author

Maity, Pradip K.

Faisal, Saqib

Rolfe, Alan

Stoianova, Diana

Hanson, Paul R.

Publisher

American Chemical Society

Type

Article

Article Version

Scholarly/refereed, author accepted manuscript

Rights

This document is the Accepted Manuscript version of a Published Work that appeared in final form in the Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/acs.joc.5b01456.

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Abstract

The syntheses of silica-supported oligomeric benzyl phosphates (Si-OBPn) and triazole phosphates (Si-OTPn) using ring-opening metathesis polymerization (ROMP) for use as efficient alkylating reagents is reported. Ease of synthesis and grafting onto the surface of norbornenyl-tagged (Nb-tagged) silica particles has been demonstrated for benzyl phosphate and triazole phosphate monomers. It is shown that these silica polymer hybrid reagents, Si-OBPn and Si-OTPn, can be used to carry out alkylation reactions with an array of different nucleophiles to afford the corresponding benzylated and (triazolyl)methylated products in good yield and high purity.

Citation

Maity, P. K., Faisal, S., Rolfe, A., Stoianova, D., & Hanson, P. R. (2015). Silica-Supported Oligomeric Benzyl Phosphate (Si-OBP) and Triazole Phosphate (Si-OTP) Alkylating Reagents. The Journal of Organic Chemistry, 80(20), 9942–9950. http://doi.org/10.1021/acs.joc.5b01456

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