(1-Bromovinyl)-MIDA boronate: A readily accessible and highly versatile building block for small molecule synthesis Dedicated to Professor Paul Wender with deepest admiration on his receipt of the 2012 Tetrahedron Prize for Creativity in Organic Chemistry

Eric M. Woerly; Jonathan E. Miller; Martin D. Burke

doi:10.1016/j.tet.2013.05.050

(1-Bromovinyl)-MIDA boronate: A readily accessible and highly versatile building block for small molecule synthesis Dedicated to Professor Paul Wender with deepest admiration on his receipt of the 2012 Tetrahedron Prize for Creativity in Organic Chemistry

Eric M. Woerly, Jonathan E. Miller, Martin D. Burke

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

Abstract

Iterative cross-coupling represents a potentially general approach for the simple, efficient, and flexible construction of a wide range of functional small molecules. In this context, (1-bromovinyl)-N-methyliminodiacetic acid (MIDA) boronate is a very useful building block for small molecule synthesis. This compound can serve as a starting material for the preparation of a wide range of 1,1-disubstituted olefin-containing MIDA boronates. This compound can also be used for the iterative cross-coupling-based synthesis of various 1,1-disubstituted olefin-containing targets. Collectively, these results contribute to the expanding generality of the MIDA boronate platform.

Original language	English (US)
Pages (from-to)	7732-7740
Number of pages	9
Journal	Tetrahedron
Volume	69
Issue number	36
DOIs	https://doi.org/10.1016/j.tet.2013.05.050
State	Published - Sep 9 2013

Keywords

1,1-Disubstituted boronates
1,1-Disubstituted olefins
Iterative cross-coupling
MIDA boronates

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Online availability

10.1016/j.tet.2013.05.050

Library availability

Discover UIUC Full Text

Fingerprint

Dive into the research topics of '(1-Bromovinyl)-MIDA boronate: A readily accessible and highly versatile building block for small molecule synthesis Dedicated to Professor Paul Wender with deepest admiration on his receipt of the 2012 Tetrahedron Prize for Creativity in Organic Chemistry'. Together they form a unique fingerprint.

Cite this

Woerly, E. M., Miller, J. E., & Burke, M. D. (2013). (1-Bromovinyl)-MIDA boronate: A readily accessible and highly versatile building block for small molecule synthesis Dedicated to Professor Paul Wender with deepest admiration on his receipt of the 2012 Tetrahedron Prize for Creativity in Organic Chemistry. Tetrahedron, 69(36), 7732-7740. https://doi.org/10.1016/j.tet.2013.05.050

(1-Bromovinyl)-MIDA boronate: A readily accessible and highly versatile building block for small molecule synthesis Dedicated to Professor Paul Wender with deepest admiration on his receipt of the 2012 Tetrahedron Prize for Creativity in Organic Chemistry. / Woerly, Eric M.; Miller, Jonathan E.; Burke, Martin D.
In: Tetrahedron, Vol. 69, No. 36, 09.09.2013, p. 7732-7740.

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

Woerly, EM, Miller, JE & Burke, MD 2013, '(1-Bromovinyl)-MIDA boronate: A readily accessible and highly versatile building block for small molecule synthesis Dedicated to Professor Paul Wender with deepest admiration on his receipt of the 2012 Tetrahedron Prize for Creativity in Organic Chemistry', Tetrahedron, vol. 69, no. 36, pp. 7732-7740. https://doi.org/10.1016/j.tet.2013.05.050

Woerly, Eric M. ; Miller, Jonathan E. ; Burke, Martin D. / (1-Bromovinyl)-MIDA boronate : A readily accessible and highly versatile building block for small molecule synthesis Dedicated to Professor Paul Wender with deepest admiration on his receipt of the 2012 Tetrahedron Prize for Creativity in Organic Chemistry. In: Tetrahedron. 2013 ; Vol. 69, No. 36. pp. 7732-7740.

@article{d49996dedef84167a28c593416b39f5c,

title = "(1-Bromovinyl)-MIDA boronate: A readily accessible and highly versatile building block for small molecule synthesis Dedicated to Professor Paul Wender with deepest admiration on his receipt of the 2012 Tetrahedron Prize for Creativity in Organic Chemistry",

abstract = "Iterative cross-coupling represents a potentially general approach for the simple, efficient, and flexible construction of a wide range of functional small molecules. In this context, (1-bromovinyl)-N-methyliminodiacetic acid (MIDA) boronate is a very useful building block for small molecule synthesis. This compound can serve as a starting material for the preparation of a wide range of 1,1-disubstituted olefin-containing MIDA boronates. This compound can also be used for the iterative cross-coupling-based synthesis of various 1,1-disubstituted olefin-containing targets. Collectively, these results contribute to the expanding generality of the MIDA boronate platform.",

keywords = "1,1-Disubstituted boronates, 1,1-Disubstituted olefins, Iterative cross-coupling, MIDA boronates",

author = "Woerly, {Eric M.} and Miller, {Jonathan E.} and Burke, {Martin D.}",

note = "Funding Information: We gratefully acknowledge the NIH for funding ( R01 GM080436 ). E.M.W. is an NSF Graduate Fellow and M.D.B. is an Early Career Scientist of the Howard Hughes Medical Institute.",

year = "2013",

month = sep,

day = "9",

doi = "10.1016/j.tet.2013.05.050",

language = "English (US)",

volume = "69",

pages = "7732--7740",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "36",

}

TY - JOUR

T1 - (1-Bromovinyl)-MIDA boronate

T2 - A readily accessible and highly versatile building block for small molecule synthesis Dedicated to Professor Paul Wender with deepest admiration on his receipt of the 2012 Tetrahedron Prize for Creativity in Organic Chemistry

AU - Woerly, Eric M.

AU - Miller, Jonathan E.

AU - Burke, Martin D.

N1 - Funding Information: We gratefully acknowledge the NIH for funding ( R01 GM080436 ). E.M.W. is an NSF Graduate Fellow and M.D.B. is an Early Career Scientist of the Howard Hughes Medical Institute.

PY - 2013/9/9

Y1 - 2013/9/9

N2 - Iterative cross-coupling represents a potentially general approach for the simple, efficient, and flexible construction of a wide range of functional small molecules. In this context, (1-bromovinyl)-N-methyliminodiacetic acid (MIDA) boronate is a very useful building block for small molecule synthesis. This compound can serve as a starting material for the preparation of a wide range of 1,1-disubstituted olefin-containing MIDA boronates. This compound can also be used for the iterative cross-coupling-based synthesis of various 1,1-disubstituted olefin-containing targets. Collectively, these results contribute to the expanding generality of the MIDA boronate platform.

AB - Iterative cross-coupling represents a potentially general approach for the simple, efficient, and flexible construction of a wide range of functional small molecules. In this context, (1-bromovinyl)-N-methyliminodiacetic acid (MIDA) boronate is a very useful building block for small molecule synthesis. This compound can serve as a starting material for the preparation of a wide range of 1,1-disubstituted olefin-containing MIDA boronates. This compound can also be used for the iterative cross-coupling-based synthesis of various 1,1-disubstituted olefin-containing targets. Collectively, these results contribute to the expanding generality of the MIDA boronate platform.

KW - 1,1-Disubstituted boronates

KW - 1,1-Disubstituted olefins

KW - Iterative cross-coupling

KW - MIDA boronates

UR - http://www.scopus.com/inward/record.url?scp=84880922822&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84880922822&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2013.05.050

DO - 10.1016/j.tet.2013.05.050

M3 - Article

AN - SCOPUS:84880922822

SN - 0040-4020

VL - 69

SP - 7732

EP - 7740

JO - Tetrahedron

JF - Tetrahedron

IS - 36

ER -

(1-Bromovinyl)-MIDA boronate: A readily accessible and highly versatile building block for small molecule synthesis Dedicated to Professor Paul Wender with deepest admiration on his receipt of the 2012 Tetrahedron Prize for Creativity in Organic Chemistry

Abstract

Keywords

ASJC Scopus subject areas

Online availability

Library availability

Related links

Fingerprint

Cite this