Ethynyl MIDA boronate: A readily accessible and highly versatile building block for small molecule synthesis

Justin R. Struble; Suk Joong Lee; Martin D. Burke

doi:10.1016/j.tet.2010.04.020

Ethynyl MIDA boronate: A readily accessible and highly versatile building block for small molecule synthesis

Justin R. Struble
, Suk Joong Lee
, Martin D. Burke

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

Abstract

Ethynyl N-methyliminodiacetic acid (MIDA) boronate is a very useful building block for small molecule synthesis. This compound can serve as both a bifunctional acetylene equivalent with the capacity for terminus-selective bis-functionalization and a versatile starting material for the preparation of a wide range of other MIDA boronate building blocks.

Original language	English (US)
Pages (from-to)	4710-4718
Number of pages	9
Journal	Tetrahedron
Volume	66
Issue number	26
DOIs	https://doi.org/10.1016/j.tet.2010.04.020
State	Published - Jun 26 2010

Keywords

Alkynes Sonogashira coupling
Diels-Alder
Iterative cross-coupling
MIDA boronates
Small molecule synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Online availability

10.1016/j.tet.2010.04.020

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@article{a1802ddc3b0f45d2a8ba2e73af3dcb5f,

title = "Ethynyl MIDA boronate: A readily accessible and highly versatile building block for small molecule synthesis",

abstract = "Ethynyl N-methyliminodiacetic acid (MIDA) boronate is a very useful building block for small molecule synthesis. This compound can serve as both a bifunctional acetylene equivalent with the capacity for terminus-selective bis-functionalization and a versatile starting material for the preparation of a wide range of other MIDA boronate building blocks.",

keywords = "Alkynes Sonogashira coupling, Diels-Alder, Iterative cross-coupling, MIDA boronates, Small molecule synthesis",

author = "Struble, \{Justin R.\} and Lee, \{Suk Joong\} and Burke, \{Martin D.\}",

note = "We gratefully acknowledge E.M. Woerly and E.P. Gillis for performing the synthesis of 7 and 8 , respectively. We also thank the NSF (CAREER 0747778 ), Howard Hughes Medical Institute , the Arnold and Mabel Beckman Foundation , and Bristol-Myers Squibb for financial support, Dr. Danielle Gray and Amy Fuller for X-ray crystallographic analysis, and Dr. Steve Mullen and Furong Sun for mass spectral analysis. M.D.B. is a Howard Hughes Medical Institute Early Career Scientist, Beckman Young Investigator, Sloan Foundation Research Fellow, Dreyfus New Faculty Awardee, Bristol-Myers Squibb Unrestricted Grant in Synthetic Organic Chemistry Awardee, Eli Lilly Grantee, Amgen Young Investigator, and AstraZeneca Excellence in Chemistry Awardee.",

year = "2010",

month = jun,

day = "26",

doi = "10.1016/j.tet.2010.04.020",

language = "English (US)",

volume = "66",

pages = "4710--4718",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "26",

}

TY - JOUR

T1 - Ethynyl MIDA boronate

T2 - A readily accessible and highly versatile building block for small molecule synthesis

AU - Struble, Justin R.

AU - Lee, Suk Joong

AU - Burke, Martin D.

N1 - We gratefully acknowledge E.M. Woerly and E.P. Gillis for performing the synthesis of 7 and 8 , respectively. We also thank the NSF (CAREER 0747778 ), Howard Hughes Medical Institute , the Arnold and Mabel Beckman Foundation , and Bristol-Myers Squibb for financial support, Dr. Danielle Gray and Amy Fuller for X-ray crystallographic analysis, and Dr. Steve Mullen and Furong Sun for mass spectral analysis. M.D.B. is a Howard Hughes Medical Institute Early Career Scientist, Beckman Young Investigator, Sloan Foundation Research Fellow, Dreyfus New Faculty Awardee, Bristol-Myers Squibb Unrestricted Grant in Synthetic Organic Chemistry Awardee, Eli Lilly Grantee, Amgen Young Investigator, and AstraZeneca Excellence in Chemistry Awardee.

PY - 2010/6/26

Y1 - 2010/6/26

N2 - Ethynyl N-methyliminodiacetic acid (MIDA) boronate is a very useful building block for small molecule synthesis. This compound can serve as both a bifunctional acetylene equivalent with the capacity for terminus-selective bis-functionalization and a versatile starting material for the preparation of a wide range of other MIDA boronate building blocks.

AB - Ethynyl N-methyliminodiacetic acid (MIDA) boronate is a very useful building block for small molecule synthesis. This compound can serve as both a bifunctional acetylene equivalent with the capacity for terminus-selective bis-functionalization and a versatile starting material for the preparation of a wide range of other MIDA boronate building blocks.

KW - Alkynes Sonogashira coupling

KW - Diels-Alder

KW - Iterative cross-coupling

KW - MIDA boronates

KW - Small molecule synthesis

UR - https://www.scopus.com/pages/publications/77954243594

UR - https://www.scopus.com/pages/publications/77954243594#tab=citedBy

U2 - 10.1016/j.tet.2010.04.020

DO - 10.1016/j.tet.2010.04.020

M3 - Article

AN - SCOPUS:77954243594

SN - 0040-4020

VL - 66

SP - 4710

EP - 4718

JO - Tetrahedron

JF - Tetrahedron

IS - 26

ER -

Ethynyl MIDA boronate: A readily accessible and highly versatile building block for small molecule synthesis

Abstract

Keywords

ASJC Scopus subject areas

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