A Mild Method for Making MIDA Boronates

Aidan M. Kelly; Peng Jui Chen; Jenna Klubnick; Daniel J. Blair; Martin D. Burke

doi:10.1021/acs.orglett.0c02449

A Mild Method for Making MIDA Boronates

Aidan M. Kelly, Peng Jui Chen, Jenna Klubnick, Daniel J. Blair, Martin D. Burke

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

Abstract

We disclose that a predried form of methyliminodiacetic acid (MIDA), MIDA anhydride, acts as both a source of the MIDA ligand and an in situ desiccant to enable a mild and simple MIDA boronate synthesis procedure. This method expands the range of sensitive boronic acids that can be converted into their MIDA boronate counterparts. Further utilizing unique properties of MIDA boronates, we have developed a MIDA Boronate Maker Kit which enables the direct preparation and purification of MIDA boronates from boronic acids using only heating and centrifuge equipment that is widely available in laboratories that do not specialize in organic synthesis.

Original language	English (US)
Pages (from-to)	9408-9414
Number of pages	7
Journal	Organic Letters
Volume	22
Issue number	24
DOIs	https://doi.org/10.1021/acs.orglett.0c02449
State	Published - Dec 18 2020

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Online availability

10.1021/acs.orglett.0c02449

Library availability

Discover UIUC Full Text

Cite this

@article{04728233f5694279b262133a7cf9e6d2,

title = "A Mild Method for Making MIDA Boronates",

abstract = "We disclose that a predried form of methyliminodiacetic acid (MIDA), MIDA anhydride, acts as both a source of the MIDA ligand and an in situ desiccant to enable a mild and simple MIDA boronate synthesis procedure. This method expands the range of sensitive boronic acids that can be converted into their MIDA boronate counterparts. Further utilizing unique properties of MIDA boronates, we have developed a MIDA Boronate Maker Kit which enables the direct preparation and purification of MIDA boronates from boronic acids using only heating and centrifuge equipment that is widely available in laboratories that do not specialize in organic synthesis.",

author = "Kelly, {Aidan M.} and Chen, {Peng Jui} and Jenna Klubnick and Blair, {Daniel J.} and Burke, {Martin D.}",

year = "2020",

month = dec,

day = "18",

doi = "10.1021/acs.orglett.0c02449",

language = "English (US)",

volume = "22",

pages = "9408--9414",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "24",

}

TY - JOUR

T1 - A Mild Method for Making MIDA Boronates

AU - Kelly, Aidan M.

AU - Chen, Peng Jui

AU - Klubnick, Jenna

AU - Blair, Daniel J.

AU - Burke, Martin D.

PY - 2020/12/18

Y1 - 2020/12/18

N2 - We disclose that a predried form of methyliminodiacetic acid (MIDA), MIDA anhydride, acts as both a source of the MIDA ligand and an in situ desiccant to enable a mild and simple MIDA boronate synthesis procedure. This method expands the range of sensitive boronic acids that can be converted into their MIDA boronate counterparts. Further utilizing unique properties of MIDA boronates, we have developed a MIDA Boronate Maker Kit which enables the direct preparation and purification of MIDA boronates from boronic acids using only heating and centrifuge equipment that is widely available in laboratories that do not specialize in organic synthesis.

AB - We disclose that a predried form of methyliminodiacetic acid (MIDA), MIDA anhydride, acts as both a source of the MIDA ligand and an in situ desiccant to enable a mild and simple MIDA boronate synthesis procedure. This method expands the range of sensitive boronic acids that can be converted into their MIDA boronate counterparts. Further utilizing unique properties of MIDA boronates, we have developed a MIDA Boronate Maker Kit which enables the direct preparation and purification of MIDA boronates from boronic acids using only heating and centrifuge equipment that is widely available in laboratories that do not specialize in organic synthesis.

UR - http://www.scopus.com/inward/record.url?scp=85090488239&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85090488239&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.0c02449

DO - 10.1021/acs.orglett.0c02449

M3 - Article

C2 - 32841037

AN - SCOPUS:85090488239

SN - 1523-7060

VL - 22

SP - 9408

EP - 9414

JO - Organic Letters

JF - Organic Letters

IS - 24

ER -

A Mild Method for Making MIDA Boronates

Abstract

ASJC Scopus subject areas

Online availability

Library availability

Related links

Fingerprint

Cite this