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

McDougal, Nolan T. and Streuff, Jan and Mukherjee, Herschel and Virgil, Scott C. and Stoltz, Brian M. (2010) Rapid synthesis of an electron-deficient t-BuPHOX ligand: cross-coupling of aryl bromides with secondary phosphine oxides. Tetrahedron Letters, 51 (42). pp. 5550-5554. ISSN 0040-4039. PMCID PMC2976555. https://resolver.caltech.edu/CaltechAUTHORS:20101103-104745366

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1016/j.tetlet.2010.08.039DOIArticle
http://www.sciencedirect.com/science/article/pii/S0040403910014590PublisherArticle
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2976555/PubMed CentralArticle
ORCID:
AuthorORCID
Virgil, Scott C.0000-0001-8586-5641
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2010 Elsevier Ltd. Received 13 May 2010; revised 11 August 2010; accepted 12 August 2010. Available online 17 August 2010. 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.
Funders:
Funding AgencyGrant Number
King Abdullah University of Science and Technology (KAUST)KUS-11-006-02
NIHR01GM080269-01
Deutscher Akademischer Austauschdienst (DAAD)UNSPECIFIED
Abbott LaboratoriesUNSPECIFIED
AmgenUNSPECIFIED
Gordon and Betty Moore FoundationUNSPECIFIED
CaltechUNSPECIFIED
Issue or Number:42
PubMed Central ID:PMC2976555
Record Number:CaltechAUTHORS:20101103-104745366
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20101103-104745366
Official Citation:Nolan T. McDougal, Jan Streuff, Herschel Mukherjee, Scott C. Virgil, Brian M. Stoltz, Rapid synthesis of an electron-deficient t-BuPHOX ligand: cross-coupling of aryl bromides with secondary phosphine oxides, Tetrahedron Letters, Volume 51, Issue 42, 20 October 2010, Pages 5550-5554, ISSN 0040-4039, http://dx.doi.org/10.1016/j.tetlet.2010.08.039. (http://www.sciencedirect.com/science/article/pii/S0040403910014590)
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:20648
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:03 Nov 2010 18:27
Last Modified:09 Mar 2020 13:19

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