Literature DB >> 21121636

Monomer-on-monomer (MoM) Mitsunobu reaction: facile purification utilizing surface-initiated sequestration.

Pradip K Maity1, Alan Rolfe, Thiwanka B Samarakoon, Saqib Faisal, Ryan D Kurtz, Toby R Long, Alexander Schätz, Daniel L Flynn, Robert N Grass, Wendelin J Stark, Oliver Reiser, Paul R Hanson.   

Abstract

A monomer-on-monomer (MoM) Mitsunobu reaction utilizing norbornenyl-tagged (Nb-tagged) reagents is reported, whereby purification was rapidly achieved by employing ring-opening metathesis polymerization, which was initiated by any of three methods utilizing Grubbs catalyst: (i) free catalyst in solution, (ii) surface-initiated catalyst-armed silica, or (iii) surface-initiated catalyst-armed Co/C magnetic nanoparticles.

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Year:  2010        PMID： 21121636      PMCID： PMC3271942          DOI： 10.1021/ol1022382

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  23 in total

1.  Immobilization on a Nanomagnetic Co/C Surface Using ROM Polymerization: Generation of a Hybrid Material as Support for a Recyclable Palladium Catalyst.

Authors:  Alexander Schätz; Toby R Long; Robert N Grass; Wendelin J Stark; Paul R Hanson; Oliver Reiser
Journal:  Adv Funct Mater       Date:  2010-12-21       Impact factor: 18.808

2.  Organocatalytic Mitsunobu reactions.

Authors:  Tracy Yuen Sze But; Patrick H Toy
Journal:  J Am Chem Soc       Date:  2006-08-02       Impact factor: 15.419

3.  Utilizing the intramolecular Fukuyama-Mitsunobu reaction for a flexible synthesis of novel heterocyclic scaffolds for peptidomimetic drug design.

Authors:  Christoph W Zapf; Juan R Del Valle; Murray Goodman
Journal:  Bioorg Med Chem Lett       Date:  2005-09-15       Impact factor: 2.823

4.  Impurity annihilation: chromatography-free parallel Mitsunobu reactions.

Authors:  A G Barrett; R S Roberts; J Schröder
Journal:  Org Lett       Date:  2000-09-21       Impact factor: 6.005

5.  Multipolymer solution-phase reactions: application to the Mitsunobu reaction.

Authors:  Andrew M Harned; Helen Song He; Patrick H Toy; Daniel L Flynn; Paul R Hanson
Journal:  J Am Chem Soc       Date:  2005-01-12       Impact factor: 15.419

6.  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

7.  Chemically-tagged Mitsunobu reagents for use in solution-phase chemical library synthesis.

Authors:  G W Starkey; J J Parlow; D L Flynn
Journal:  Bioorg Med Chem Lett       Date:  1998-09-08       Impact factor: 2.823

8.  Second-generation tags for fluorous chemistry exemplified with a new fluorous Mitsunobu reagent.

Authors:  Qianli Chu; Christopher Henry; Dennis P Curran
Journal:  Org Lett       Date:  2008-05-17       Impact factor: 6.005

9.  High-load, oligomeric dichlorotriazine: a versatile ROMP-derived reagent and scavenger.

Authors:  Alan Rolfe; Donald A Probst; Kelly A Volp; Iman Omar; Daniel L Flynn; Paul R Hanson
Journal:  J Org Chem       Date:  2008-10-21       Impact factor: 4.354

10.  Parallel synthesis of terminal alkynes using a ROMPgel-supported ethyl 1-diazo-2-oxopropylphosphonate.

Authors:  Anthony G M Barrett; Brian T Hopkins; Andrew C Love; Livio Tedeschi
Journal:  Org Lett       Date:  2004-03-04       Impact factor: 6.005
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  9 in total

1.  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

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

Authors:  Pradip K Maity; Saqib Faisal; Alan Rolfe; Diana Stoianova; Paul R Hanson
Journal:  J Org Chem       Date:  2015-10-02       Impact factor: 4.354

3.  Intramolecular monomer-on-monomer (MoM) Mitsunobu cyclization for the synthesis of benzofused thiadiazepine-dioxides.

Authors:  Pradip K Maity; Quirin M Kainz; Saqib Faisal; Alan Rolfe; Thiwanka B Samarakoon; Fatima Z Basha; Oliver Reiser; Paul R Hanson
Journal:  Chem Commun (Camb)       Date:  2011-10-26       Impact factor: 6.222

4.  "Click"-capture, ring-opening metathesis polymerization (ROMP), release: facile triazolation utilizing ROMP-derived oligomeric phosphates.

Authors:  Toby R Long; Saqib Faisal; Pradip K Maity; Alan Rolfe; Ryan Kurtz; Sarra V Klimberg; Muhammad-Rabbie Najjar; Fatima Z Basha; Paul R Hanson
Journal:  Org Lett       Date:  2011-03-24       Impact factor: 6.005

5.  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

6.  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

7.  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

8.  Advances and mechanistic insight on the catalytic Mitsunobu reaction using recyclable azo reagents.

Authors:  Daisuke Hirose; Martin Gazvoda; Janez Košmrlj; Tsuyoshi Taniguchi
Journal:  Chem Sci       Date:  2016-04-13       Impact factor: 9.825

9.  Magnetic Nanobeads as Support for Zinc(II)-Cyclen Complexes: Selective and Reversible Extraction of Riboflavin.

Authors:  Quirin M Kainz; Andreas Späth; Stefan Weiss; Thomas D Michl; Alexander Schätz; Wendelin J Stark; Burkhard König; Oliver Reiser
Journal:  ChemistryOpen       Date:  2012-06-11       Impact factor: 2.911
  9 in total

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