Monomer-on-monomer (MoM) Mitsunobu Reaction: Facile Purification Utilizing Surface-initiated Sequestration

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2010 Dec 3

PMID 21121636

Citations 9

Authors

Pradip K Maity

Alan Rolfe

Thiwanka B Samarakoon

Saqib Faisal

Ryan D Kurtz

Toby R Long

Alexander Schatz

Daniel L Flynn

Robert N Grass

Wendelin J Stark

Oliver Reiser

Paul R Hanson

Affiliations

Soon will be listed here.

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.

Citing Articles

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

Hirose D, Gazvoda M, Kosmrlj J, Taniguchi T Chem Sci. 2018; 7(8):5148-5159.

PMID: 30155165 PMC: 6020523. DOI: 10.1039/c6sc00308g.

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

Faisal S, Zang Q, Maity P, Brandhofer A, Kearney P, Reiser O Org Lett. 2017; 19(9):2274-2277.

PMID: 28437113 PMC: 5595701. DOI: 10.1021/acs.orglett.7b00792.

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

Faisal S, Maity P, Zang Q, Rolfe A, Hanson P ACS Comb Sci. 2016; 18(7):394-8.

PMID: 27300761 PMC: 4943333. DOI: 10.1021/acscombsci.6b00042.

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

Faisal S, Maity P, Zang Q, Samarakoon T, Sourk R, Hanson P ACS Comb Sci. 2016; 18(7):387-93.

PMID: 27300570 PMC: 4943330. DOI: 10.1021/acscombsci.6b00041.

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

Maity P, Faisal S, Rolfe A, Stoianova D, Hanson P J Org Chem. 2015; 80(20):9942-50.

PMID: 26430955 PMC: 4848109. DOI: 10.1021/acs.joc.5b01456.

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