Literature DB >> 26430955

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

Pradip K Maity1,2, Saqib Faisal1,2, Alan Rolfe1,2, Diana Stoianova3, Paul R Hanson1,2.   

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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Year:  2015        PMID： 26430955      PMCID： PMC4848109          DOI： 10.1021/acs.joc.5b01456

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  70 in total

1.  Homogeneous Metathesis Polymerization by Well-Defined Group VI and Group VIII Transition-Metal Alkylidenes: Fundamentals and Applications in the Preparation of Advanced Materials.

Authors:  M R Buchmeiser
Journal:  Chem Rev       Date:  2000-04-12       Impact factor: 60.622

2.  Multi-step application of immobilized reagents and scavengers: a total synthesis of epothilone C.

Authors:  R Ian Storer; Toshiyasu Takemoto; Philip S Jackson; Dearg S Brown; Ian R Baxendale; Steven V Ley
Journal:  Chemistry       Date:  2004-05-17       Impact factor: 5.236

3.  Synthesis and library construction of privileged tetra-substituted Δ5-2-oxopiperazine as β-turn structure mimetics.

Authors:  Jonghoon Kim; Won Seok Lee; Jaeyoung Koo; Jeongae Lee; Seung Bum Park
Journal:  ACS Comb Sci       Date:  2013-11-26       Impact factor: 3.784

4.  Total synthesis of the amaryllidaceae alkaloid (+)-plicamine and its unnatural enantiomer by using solid-supported reagents and scavengers in a multistep sequence of reactions.

Authors:  Ian R Baxendale; Steven V Ley; Claudia Piutti
Journal:  Angew Chem Int Ed Engl       Date:  2002-06-17       Impact factor: 15.336

5.  Reduction of azides to primary amines in substrates bearing labile ester functionality. Synthesis of a PEG-solubilized, "Y"-shaped iminodiacetic acid reagent for preparation of folate-tethered drugs.

Authors:  J W Lee; P L Fuchs
Journal:  Org Lett       Date:  1999-07-29       Impact factor: 6.005

6.  Synthesis of epoxybenzo[d]isothiazole 1,1-dioxides via a reductive-Heck, metathesis-sequestration protocol.

Authors:  Naeem Asad; Paul R Hanson; Toby R Long; Dinesh K Rayabarapu; Alan Rolfe
Journal:  Chem Commun (Camb)       Date:  2011-07-05       Impact factor: 6.222

7.  High-load, hybrid Si-ROMP reagents.

Authors:  Alan Rolfe; Joanna K Loh; Pradip K Maity; Paul R Hanson
Journal:  Org Lett       Date:  2010-12-01       Impact factor: 6.005

8.  Silica-immobilized chiral dirhodium(II) catalyst for enantioselective carbenoid reactions.

Authors:  Kathryn M Chepiga; Yan Feng; Nicholas A Brunelli; Christopher W Jones; Huw M L Davies
Journal:  Org Lett       Date:  2013-11-19       Impact factor: 6.005

9.  Ring-opening metathesis polymer sphere-supported seco-porphyrazines: efficient and recyclable photooxygenation catalysts.

Authors:  Matthew J Fuchter; Brian M Hoffman; Anthony G M Barrett
Journal:  J Org Chem       Date:  2006-01-20       Impact factor: 4.354

10.  Surface functionalization of silica by Si-H activation of hydrosilanes.

Authors:  Nirmalya Moitra; Shun Ichii; Toshiyuki Kamei; Kazuyoshi Kanamori; Yang Zhu; Kazuyuki Takeda; Kazuki Nakanishi; Toyoshi Shimada
Journal:  J Am Chem Soc       Date:  2014-08-07       Impact factor: 15.419
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  3 in total

1.  Development and Application of a Recyclable High-Load Magnetic Co/C Hybrid ROMP-Derived Benzenesulfonyl Chloride Reagent and Utility of Corresponding Analogues.

Authors:  Saqib Faisal; Qin Zang; Pradip K Maity; Agnes Brandhofer; Patrick C Kearney; Oliver Reiser; Robert N Grass; Diana Stoianova; Paul R Hanson
Journal:  Org Lett       Date:  2017-04-24       Impact factor: 6.005

2.  Synthesis of High-Load, Hybrid Silica-Immobilized Heterocyclic Benzyl Phosphate (Si-OHBP) and Triazolyl Phosphate (Si-OHTP) Alkylating Reagents.

Authors:  Saqib Faisal; Pradip K Maity; Qin Zang; Alan Rolfe; Paul R Hanson
Journal:  ACS Comb Sci       Date:  2016-06-14       Impact factor: 3.784

3.  Application of Silica-Supported Alkylating Reagents in a One-Pot, Sequential Protocol to Diverse Benzoxathiazepine 1,1-Dioxides.

Authors:  Saqib Faisal; Pradip K Maity; Qin Zang; Thiwanka B Samarakoon; Robert L Sourk; Paul R Hanson
Journal:  ACS Comb Sci       Date:  2016-06-14       Impact factor: 3.784
  3 in total

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