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Use of in Situ Isopropoxide Protection in the Metal−Halogen Exchange of Arylboronates
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Abstract
Isopropoxide protection of arylboronates allowed their use in metal−halogen exchange reactions. The isopropoxide-protected borate species were obtained from a boronate or in situ from dibromoarenes. meta- and para-dibromoarenes were converted via these intermediates into functionalized arylboronates in a one-pot manner.
Citing Articles
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This article has been cited by 4 ACS Journal articles (4 most recent appear below).
Gold(III)-Catalyzed Halogenation of Aromatic Boronates with N-Halosuccinimides
Di Qiu, Fanyang Mo, Zhitong Zheng, Yan Zhang, and Jianbo WangOrganic Letters2010 12 (23), 5474-5477Gold(III)-Catalyzed Halogenation of Aromatic Boronates with N-Halosuccinimides
Di Qiu, Fanyang Mo, Zhitong Zheng, Yan Zhang, and Jianbo WangOrganic Letters2010 12 (23), 5474-5477Aromatic boronates bearing halogen substituents in the aromatic ring can be synthesized by AuCl3-catalyzed halogenations with N-halosuccinimides.
Alkyne [3 + 2] Cycloadditions of Iodosydnones Toward Functionalized 1,3,5-Trisubstituted Pyrazoles
Duncan L. Browne, John B. Taylor, Andrew Plant and Joseph P. A. HarrityThe Journal of Organic Chemistry2010 75 (3), 984-987Alkyne [3 + 2] Cycloadditions of Iodosydnones Toward Functionalized 1,3,5-Trisubstituted Pyrazoles
Duncan L. Browne, John B. Taylor, Andrew Plant and Joseph P. A. HarrityThe Journal of Organic Chemistry2010 75 (3), 984-987The cycloaddition of 4-iodosydnones with terminal alkynes proceeds with excellent regiocontrol to provide 5-iodo pyrazoles. These products participate smoothly in subsequent C−C and C−heteroatom bond forming processes.
Practical Aspects of Carbon−Carbon Cross-Coupling Reactions Using Heteroarenes
Vincent F. Slagt, André H. M. de Vries, Johannes G. de Vries and Richard M. KelloggOrganic Process Research & Development2010 14 (1), 30-47Practical Aspects of Carbon−Carbon Cross-Coupling Reactions Using Heteroarenes
Vincent F. Slagt, André H. M. de Vries, Johannes G. de Vries and Richard M. KelloggOrganic Process Research & Development2010 14 (1), 30-47The use of cross-coupling reactions for the preparation of alkylated and arylated heteroaromatic compounds has increased tremendously over the past two decades. This has been driven on the one hand by the increasingly complex structures of new drugs, most ...
Investigation of the Scope and Regiochemistry of Alkynylboronate Cycloadditions with Sydnones
Duncan L. Browne, Jérôme F. Vivat, Andrew Plant, Enrique Gomez-Bengoa and Joseph P. A. HarrityJournal of the American Chemical Society2009 131 (22), 7762-7769Investigation of the Scope and Regiochemistry of Alkynylboronate Cycloadditions with Sydnones
Duncan L. Browne, Jérôme F. Vivat, Andrew Plant, Enrique Gomez-Bengoa and Joseph P. A. HarrityJournal of the American Chemical Society2009 131 (22), 7762-7769The cycloaddition of alkynylboronates and sydnones provides a convenient and highly regioselective method for the synthesis of a broad range of di-, tri-, and tetrasubstituted pyrazole boronic esters. The origins of an observed regiochemical divergence in ...
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History
- Published In Issue August 17, 2007
- Received May 16, 2007
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