Rapid synthesis of an electron-deficient t-BuPHOX ligand: cross-coupling of aryl bromides with secondary phosphine oxides

Handle URI:
http://hdl.handle.net/10754/599445
Title:
Rapid synthesis of an electron-deficient t-BuPHOX ligand: cross-coupling of aryl bromides with secondary phosphine oxides
Authors:
McDougal, Nolan T.; Streuff, Jan; Mukherjee, Herschel; Virgil, Scott C.; Stoltz, Brian M.
Abstract:
Herein an efficient and direct copper-catalyzed coupling of oxazoline-containing aryl bromides with electron-deficient secondary phosphine oxides is reported. The resulting tertiary phosphine oxides can be reduced to prepare a range of PHOX ligands. The presented strategy is a useful alternative to known methods for constructing PHOX derivatives.
Citation:
McDougal NT, Streuff J, Mukherjee H, Virgil SC, Stoltz BM (2010) Rapid synthesis of an electron-deficient t-BuPHOX ligand: cross-coupling of aryl bromides with secondary phosphine oxides. Tetrahedron Letters 51: 5550–5554. Available: http://dx.doi.org/10.1016/j.tetlet.2010.08.039.
Publisher:
Elsevier BV
Journal:
Tetrahedron Letters
KAUST Grant Number:
KUS-11-006-02
Issue Date:
Oct-2010
DOI:
10.1016/j.tetlet.2010.08.039
PubMed ID:
21076623
PubMed Central ID:
PMC2976555
Type:
Article
ISSN:
0040-4039
Sponsors:
This publication is based on the work supported by Award No. KUS-11-006-02, made by King Abdullah University of Science and Technology (KAUST). Additionally, the authors wish to thank NIH-NIGMS (R01 GM 080269-01), the German Academic Exchange Service (DAAD, postdoctoral fellowship to J.S.), Abbott Laboratories, Amgen, the Gordon and Betty Moore Foundation, and Caltech for financial support.
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Full metadata record

DC FieldValue Language
dc.contributor.authorMcDougal, Nolan T.en
dc.contributor.authorStreuff, Janen
dc.contributor.authorMukherjee, Herschelen
dc.contributor.authorVirgil, Scott C.en
dc.contributor.authorStoltz, Brian M.en
dc.date.accessioned2016-02-28T05:51:16Zen
dc.date.available2016-02-28T05:51:16Zen
dc.date.issued2010-10en
dc.identifier.citationMcDougal NT, Streuff J, Mukherjee H, Virgil SC, Stoltz BM (2010) Rapid synthesis of an electron-deficient t-BuPHOX ligand: cross-coupling of aryl bromides with secondary phosphine oxides. Tetrahedron Letters 51: 5550–5554. Available: http://dx.doi.org/10.1016/j.tetlet.2010.08.039.en
dc.identifier.issn0040-4039en
dc.identifier.pmid21076623en
dc.identifier.doi10.1016/j.tetlet.2010.08.039en
dc.identifier.urihttp://hdl.handle.net/10754/599445en
dc.description.abstractHerein an efficient and direct copper-catalyzed coupling of oxazoline-containing aryl bromides with electron-deficient secondary phosphine oxides is reported. The resulting tertiary phosphine oxides can be reduced to prepare a range of PHOX ligands. The presented strategy is a useful alternative to known methods for constructing PHOX derivatives.en
dc.description.sponsorshipThis publication is based on the work supported by Award No. KUS-11-006-02, made by King Abdullah University of Science and Technology (KAUST). Additionally, the authors wish to thank NIH-NIGMS (R01 GM 080269-01), the German Academic Exchange Service (DAAD, postdoctoral fellowship to J.S.), Abbott Laboratories, Amgen, the Gordon and Betty Moore Foundation, and Caltech for financial support.en
dc.publisherElsevier BVen
dc.titleRapid synthesis of an electron-deficient t-BuPHOX ligand: cross-coupling of aryl bromides with secondary phosphine oxidesen
dc.typeArticleen
dc.identifier.journalTetrahedron Lettersen
dc.identifier.pmcidPMC2976555en
dc.contributor.institutionThe Arnold and Mabel Beckman Laboratories of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, United States.en
kaust.grant.numberKUS-11-006-02en
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