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

Nolan T. McDougal; Jan Streuff; Herschel Mukherjee; Scott C. Virgil; Brian M. Stoltz

doi:10.1016/j.tetlet.2010.08.039

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

Nolan T. McDougal, Jan Streuff, Herschel Mukherjee, Scott C. Virgil, Brian M. Stoltz

Research output: Contribution to journal › Article › peer-review

67 Scopus citations

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.

Original language	English (US)
Pages (from-to)	5550-5554
Number of pages	5
Journal	Tetrahedron Letters
Volume	51
Issue number	42
DOIs	https://doi.org/10.1016/j.tetlet.2010.08.039
State	Published - Oct 2010
Externally published	Yes

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledged KAUST grant number(s): KUS-11-006-02
Acknowledgements: 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.
This publication acknowledges KAUST support, but has no KAUST affiliated authors.

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10.1016/j.tetlet.2010.08.039

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

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.",

author = "McDougal, {Nolan T.} and Jan Streuff and Herschel Mukherjee and Virgil, {Scott C.} and Stoltz, {Brian M.}",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledged KAUST grant number(s): KUS-11-006-02 Acknowledgements: 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. This publication acknowledges KAUST support, but has no KAUST affiliated authors.",

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doi = "10.1016/j.tetlet.2010.08.039",

language = "English (US)",

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T1 - Rapid synthesis of an electron-deficient t-BuPHOX ligand: cross-coupling of aryl bromides with secondary phosphine oxides

AU - McDougal, Nolan T.

AU - Streuff, Jan

AU - Mukherjee, Herschel

AU - Virgil, Scott C.

AU - Stoltz, Brian M.

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledged KAUST grant number(s): KUS-11-006-02 Acknowledgements: 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. This publication acknowledges KAUST support, but has no KAUST affiliated authors.

PY - 2010/10

Y1 - 2010/10

N2 - 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.

AB - 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.

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DO - 10.1016/j.tetlet.2010.08.039

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 42

ER -

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

Abstract

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