Development of practical methodologies for the synthesis of functionalized benzoboroxoles

J. Sravan Kumar; Christopher M. Bashian; Michael A. Corsello; Subash C. Jonnalagadda; Venkatram R. Mereddy

doi:10.1016/j.tetlet.2010.06.077

Development of practical methodologies for the synthesis of functionalized benzoboroxoles

J. Sravan Kumar, Christopher M. Bashian, Michael A. Corsello, Subash C. Jonnalagadda, Venkatram R. Mereddy

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

17 Scopus citations

Abstract

2-Formylphenylboronic acids upon reaction with activated olefins such as acrylates, methyl vinyl ketone, and acrylonitrile provide functionalized benzoboroxoles. The corresponding homologated benzoboroxoles were synthesized via the reaction of 2-formylphenylboronic acids with α- bromomethylacrylates.

Original language	English (US)
Pages (from-to)	4482-4485
Number of pages	4
Journal	Tetrahedron Letters
Volume	51
Issue number	34
DOIs	https://doi.org/10.1016/j.tetlet.2010.06.077
State	Published - Aug 25 2010

Bibliographical note

Funding Information:
We thank the Departments of Chemistry and Biochemistry, University of Minnesota Duluth and Rowan University for the facilities and funding. Partial support for this work was also provided by research grants from the National Institutes of Health ( CA129993 ) (V.R.M.), Whiteside Institute for Clinical Research (V.R.M.), and Rowan University Non-Salary Financial Support Grants (NSFSG) (S.C.J.). We thank Dr. Victor G. Young, Jr. (University of Minnesota X-ray Crystallographic Laboratory) for providing the crystal structure.

Keywords

Barbier allylation
Baylis-Hillman reaction
Benzoboroxoles

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10.1016/j.tetlet.2010.06.077

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title = "Development of practical methodologies for the synthesis of functionalized benzoboroxoles",

abstract = "2-Formylphenylboronic acids upon reaction with activated olefins such as acrylates, methyl vinyl ketone, and acrylonitrile provide functionalized benzoboroxoles. The corresponding homologated benzoboroxoles were synthesized via the reaction of 2-formylphenylboronic acids with α- bromomethylacrylates.",

keywords = "Barbier allylation, Baylis-Hillman reaction, Benzoboroxoles",

author = "Kumar, {J. Sravan} and Bashian, {Christopher M.} and Corsello, {Michael A.} and Jonnalagadda, {Subash C.} and Mereddy, {Venkatram R.}",

note = "Funding Information: We thank the Departments of Chemistry and Biochemistry, University of Minnesota Duluth and Rowan University for the facilities and funding. Partial support for this work was also provided by research grants from the National Institutes of Health ( CA129993 ) (V.R.M.), Whiteside Institute for Clinical Research (V.R.M.), and Rowan University Non-Salary Financial Support Grants (NSFSG) (S.C.J.). We thank Dr. Victor G. Young, Jr. (University of Minnesota X-ray Crystallographic Laboratory) for providing the crystal structure.",

year = "2010",

month = aug,

day = "25",

doi = "10.1016/j.tetlet.2010.06.077",

language = "English (US)",

volume = "51",

pages = "4482--4485",

journal = "Tetrahedron Letters",

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T1 - Development of practical methodologies for the synthesis of functionalized benzoboroxoles

AU - Kumar, J. Sravan

AU - Bashian, Christopher M.

AU - Corsello, Michael A.

AU - Jonnalagadda, Subash C.

AU - Mereddy, Venkatram R.

N1 - Funding Information: We thank the Departments of Chemistry and Biochemistry, University of Minnesota Duluth and Rowan University for the facilities and funding. Partial support for this work was also provided by research grants from the National Institutes of Health ( CA129993 ) (V.R.M.), Whiteside Institute for Clinical Research (V.R.M.), and Rowan University Non-Salary Financial Support Grants (NSFSG) (S.C.J.). We thank Dr. Victor G. Young, Jr. (University of Minnesota X-ray Crystallographic Laboratory) for providing the crystal structure.

PY - 2010/8/25

Y1 - 2010/8/25

N2 - 2-Formylphenylboronic acids upon reaction with activated olefins such as acrylates, methyl vinyl ketone, and acrylonitrile provide functionalized benzoboroxoles. The corresponding homologated benzoboroxoles were synthesized via the reaction of 2-formylphenylboronic acids with α- bromomethylacrylates.

AB - 2-Formylphenylboronic acids upon reaction with activated olefins such as acrylates, methyl vinyl ketone, and acrylonitrile provide functionalized benzoboroxoles. The corresponding homologated benzoboroxoles were synthesized via the reaction of 2-formylphenylboronic acids with α- bromomethylacrylates.

KW - Barbier allylation

KW - Baylis-Hillman reaction

KW - Benzoboroxoles

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DO - 10.1016/j.tetlet.2010.06.077

M3 - Article

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SN - 0040-4039

VL - 51

SP - 4482

EP - 4485

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 34

ER -

Development of practical methodologies for the synthesis of functionalized benzoboroxoles

Abstract

Bibliographical note

Keywords

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