Direct Chan–Lam amination and etherification of aryl BMIDA reagents

John Halford-McGuff; Eva Marie Israel; Matthew West; Julien Christian  Vantourout; Allan J. B. Watson

doi:10.1002/ejoc.202200993

Direct Chan–Lam amination and etherification of aryl BMIDA reagents

John Halford-McGuff, Eva Marie Israel, Matthew West, Julien Christian Vantourout, Allan J. B. Watson^*

^*Corresponding author for this work

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

4 Citations (Scopus)

9 Downloads (Pure)

Abstract

We report the development of a method for the direct Chan–Lam coupling of arylboronic acid N-methyliminodiacetic acid esters (ArBMIDA) with amine and alcohol nucleophiles. A wide range of C–N and C–O cross-coupled products in 34–99% yield (34 examples). This method serves to expand the scope of organoboron components that can be used directly in this oxidative coupling reaction and provides opportunities for streamlining synthesis.

Original language	English
Article number	e202200993
Number of pages	4
Journal	European Journal of Organic Chemistry
Volume	2022
Issue number	45
Early online date	2 Dec 2022
DOIs	https://doi.org/10.1002/ejoc.202200993
Publication status	Published - 6 Dec 2022

Keywords

Amination
Boron
Copper
Cross-coupling
Etherification

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10.1002/ejoc.202200993Licence: CC BY

Halford-McGuff_2022_EJOC_Chan-Lam_CC
Copyright © 2022 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
Final published version, 4.51 MBLicence: CC BY

1 Finished
1 Active

EaSI-CAT - IBioIC Industry Contribution: EaSI-CAT - IBioIC Industry Contribution
Smith, A. D. (PI)
IBioIC
1/08/21 → 30/09/27
Project: Standard
A biochemical boron tagging stategy: A biochemical boron tagging strategy for biomolecule visualisation and profiling
Watson, A. J. B. (PI)
The Leverhulme Trust
1/09/22 → 31/08/24
Project: Fellowship

Dataset underpinning "Direct Chan–Lam amination and etherification of aryl BMIDA reagents"
Watson, A. J. B. (Creator), University of St Andrews, 8 Dec 2022
DOI: 10.17630/f842a14f-2843-4266-aa37-64edc78433b9
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File

Cite this

@article{1b98124e93f64cd4868146c92b28b613,

title = "Direct Chan–Lam amination and etherification of aryl BMIDA reagents",

abstract = "We report the development of a method for the direct Chan–Lam coupling of arylboronic acid N-methyliminodiacetic acid esters (ArBMIDA) with amine and alcohol nucleophiles. A wide range of C–N and C–O cross-coupled products in 34–99% yield (34 examples). This method serves to expand the scope of organoboron components that can be used directly in this oxidative coupling reaction and provides opportunities for streamlining synthesis.",

keywords = "Amination, Boron, Copper, Cross-coupling, Etherification",

author = "John Halford-McGuff and Israel, {Eva Marie} and Matthew West and Vantourout, {Julien Christian} and Watson, {Allan J. B.}",

note = "Funding: Engineering and Physical Sciences Research Council; University of St Andrews; Leverhulme Trust (GrantNumber(s): RF-2022-014).",

year = "2022",

month = dec,

day = "6",

doi = "10.1002/ejoc.202200993",

language = "English",

volume = "2022",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH, Weinheim",

number = "45",

}

TY - JOUR

T1 - Direct Chan–Lam amination and etherification of aryl BMIDA reagents

AU - Halford-McGuff, John

AU - Israel, Eva Marie

AU - West, Matthew

AU - Vantourout, Julien Christian

AU - Watson, Allan J. B.

N1 - Funding: Engineering and Physical Sciences Research Council; University of St Andrews; Leverhulme Trust (GrantNumber(s): RF-2022-014).

PY - 2022/12/6

Y1 - 2022/12/6

N2 - We report the development of a method for the direct Chan–Lam coupling of arylboronic acid N-methyliminodiacetic acid esters (ArBMIDA) with amine and alcohol nucleophiles. A wide range of C–N and C–O cross-coupled products in 34–99% yield (34 examples). This method serves to expand the scope of organoboron components that can be used directly in this oxidative coupling reaction and provides opportunities for streamlining synthesis.

AB - We report the development of a method for the direct Chan–Lam coupling of arylboronic acid N-methyliminodiacetic acid esters (ArBMIDA) with amine and alcohol nucleophiles. A wide range of C–N and C–O cross-coupled products in 34–99% yield (34 examples). This method serves to expand the scope of organoboron components that can be used directly in this oxidative coupling reaction and provides opportunities for streamlining synthesis.

KW - Amination

KW - Boron

KW - Copper

KW - Cross-coupling

KW - Etherification

U2 - 10.1002/ejoc.202200993

DO - 10.1002/ejoc.202200993

M3 - Article

SN - 1434-193X

VL - 2022

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 45

M1 - e202200993

ER -

Direct Chan–Lam amination and etherification of aryl BMIDA reagents

Abstract

Keywords

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Projects

EaSI-CAT - IBioIC Industry Contribution: EaSI-CAT - IBioIC Industry Contribution

A biochemical boron tagging stategy: A biochemical boron tagging strategy for biomolecule visualisation and profiling

Datasets

Dataset underpinning "Direct Chan–Lam amination and etherification of aryl BMIDA reagents"

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