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. 2015 Oct 16;80(20):9942-50.
doi: 10.1021/acs.joc.5b01456. Epub 2015 Oct 2.

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

Pradip K Maity  1   2 , Saqib Faisal  1   2 , Alan Rolfe  1   2 , Diana Stoianova  3 , Paul R Hanson  1   2
Affiliations

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

Pradip K Maity et al. J Org Chem. .

Abstract

The syntheses of silica-supported oligomeric benzyl phosphates (Si-OBP(n)) and triazole phosphates (Si-OTP(n)) 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-OBP(n) and Si-OTP(n), 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.

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Figures

Figure 1
Figure 1
SEM images of Si-Nb (left), Si-OBPn (middle) and Si-OTPn (right).
Figure 2
Figure 2
Various silica-supported Oligomeric Benzyl Phosphate (Si-OBPn) analogs.
Figure 3
Figure 3
Various silica-supported Oligomeric Triazole Phosphate (Si-OTPn) analogs.
Scheme 1
Scheme 1
Synthesis of silica-supported Oligomeric Benzyl Phosphate (Si-OBPn).
Scheme 2
Scheme 2
Synthesis of silica-supported Oligomeric Triazole Phosphate (Si-OTPn).
See this image and copyright information in PMC

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