Borylation–reduction–borylation for the formation of 1,4-azaborines

Shantaram S. Kothavale; Saqib A. Iqbal; Emily L. Hanover; Abhishek K. Gupta; Eli Zysman-Colman; Michael J. Ingleson

doi:10.1021/acs.orglett.3c03731

Borylation–reduction–borylation for the formation of 1,4-azaborines

Shantaram S. Kothavale, Saqib A. Iqbal, Emily L. Hanover, Abhishek K. Gupta, Eli Zysman-Colman^*, Michael J. Ingleson^*

^*Corresponding author for this work

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

Abstract

Given the current interest in materials containing 1,4-azaborine units, the development of new routes to these structures is important. Carbonyl directed electrophilic borylation using BBr₃ is a facile method for the ortho-borylation of N,N-diaryl-amide derivatives. Subsequent addition of Et₃SiH results in carbonyl reduction and then formation of 1,4-azaborines that can be protected in situ using a Grignard reagent. Overall, borylation–reduction–borylation is a one-pot methodology to access 1,4-azaborines from simple precursors.

Original language	English
Pages (from-to)	8912-8916
Number of pages	5
Journal	Organic Letters
Volume	25
Issue number	49
Early online date	6 Dec 2023
DOIs	https://doi.org/10.1021/acs.orglett.3c03731
Publication status	Published - 15 Dec 2023

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10.1021/acs.orglett.3c03731Licence: CC BY

Kothavale_2023_OL_Borylation_CCBY
Copyright © 2023 The Authors. Open Access. Published by American Chemical Society. This publication is licensed under Creative Commons Attribution 4.0 International licence, CC-BY 4.0. To view, visit: https://creativecommons.org/licenses/by/4.0/ .
Final published version, 1.25 MBLicence: CC BY

Allan Watson Programme Grant: Boron: Beyond the Reagent
Watson, A. J. B. (PI), Morris, R. E. (CoI), Smith, A. D. (CoI) & Zysman-Colman, E. (CoI)
UK Research and Innovation
1/05/23 → 30/04/28
Project: Standard
Going Deeper with Boron: Near-infrared emitting TADF materials based on very strong organoboron acceptors
Zysman-Colman, E. (PI)
The Leverhulme Trust
1/07/22 → 31/08/26
Project: Standard

Borylation-Reduction-Borylation for the formation of 1,4-azaborines (dataset)
Kothavale, S. S. (Creator), Iqbal, S. A. (Creator), Hanover, E. L. (Creator), Gupta, A. K. (Creator), Zysman-Colman, E. (Creator) & Ingleson, M. J. (Creator), University of St Andrews, 18 Dec 2023
DOI: 10.17630/d5437e72-5005-4808-9964-dfdef6adc068
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Cite this

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title = "Borylation–reduction–borylation for the formation of 1,4-azaborines",

abstract = "Given the current interest in materials containing 1,4-azaborine units, the development of new routes to these structures is important. Carbonyl directed electrophilic borylation using BBr3 is a facile method for the ortho-borylation of N,N-diaryl-amide derivatives. Subsequent addition of Et3SiH results in carbonyl reduction and then formation of 1,4-azaborines that can be protected in situ using a Grignard reagent. Overall, borylation–reduction–borylation is a one-pot methodology to access 1,4-azaborines from simple precursors.",

author = "Kothavale, {Shantaram S.} and Iqbal, {Saqib A.} and Hanover, {Emily L.} and Gupta, {Abhishek K.} and Eli Zysman-Colman and Ingleson, {Michael J.}",

note = "This project has received funding from the Leverhulme Trust (grant Number RPG-2022-032) and the European Research Council (ERC) under the European Union{\textquoteright}s Horizon 2020 research and innovation program (Grant Agreement No. 769599). M.J.I. and E.Z.-C. also thank the EPSRC Programme Grant “Boron: Beyond the Reagent” (EP/W007517/1) for support.",

year = "2023",

month = dec,

day = "15",

doi = "10.1021/acs.orglett.3c03731",

language = "English",

volume = "25",

pages = "8912--8916",

journal = "Organic Letters",

issn = "1523-7060",

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TY - JOUR

T1 - Borylation–reduction–borylation for the formation of 1,4-azaborines

AU - Kothavale, Shantaram S.

AU - Iqbal, Saqib A.

AU - Hanover, Emily L.

AU - Gupta, Abhishek K.

AU - Zysman-Colman, Eli

AU - Ingleson, Michael J.

N1 - This project has received funding from the Leverhulme Trust (grant Number RPG-2022-032) and the European Research Council (ERC) under the European Union’s Horizon 2020 research and innovation program (Grant Agreement No. 769599). M.J.I. and E.Z.-C. also thank the EPSRC Programme Grant “Boron: Beyond the Reagent” (EP/W007517/1) for support.

PY - 2023/12/15

Y1 - 2023/12/15

N2 - Given the current interest in materials containing 1,4-azaborine units, the development of new routes to these structures is important. Carbonyl directed electrophilic borylation using BBr3 is a facile method for the ortho-borylation of N,N-diaryl-amide derivatives. Subsequent addition of Et3SiH results in carbonyl reduction and then formation of 1,4-azaborines that can be protected in situ using a Grignard reagent. Overall, borylation–reduction–borylation is a one-pot methodology to access 1,4-azaborines from simple precursors.

AB - Given the current interest in materials containing 1,4-azaborine units, the development of new routes to these structures is important. Carbonyl directed electrophilic borylation using BBr3 is a facile method for the ortho-borylation of N,N-diaryl-amide derivatives. Subsequent addition of Et3SiH results in carbonyl reduction and then formation of 1,4-azaborines that can be protected in situ using a Grignard reagent. Overall, borylation–reduction–borylation is a one-pot methodology to access 1,4-azaborines from simple precursors.

U2 - 10.1021/acs.orglett.3c03731

DO - 10.1021/acs.orglett.3c03731

M3 - Article

SN - 1523-7060

VL - 25

SP - 8912

EP - 8916

JO - Organic Letters

JF - Organic Letters

IS - 49

ER -

Borylation–reduction–borylation for the formation of 1,4-azaborines

Abstract

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Projects

Allan Watson Programme Grant: Boron: Beyond the Reagent

Going Deeper with Boron: Near-infrared emitting TADF materials based on very strong organoboron acceptors

Datasets

Borylation-Reduction-Borylation for the formation of 1,4-azaborines (dataset)

Cite this