Pyridine-promoted dediazoniation of aryldiazonium tetrafluoroborates: application to the synthesis of SF5-substituted phenylboronic esters and iodobenzenes

George Iakobson; Junyi Du; Alexandra Martha Zoya Slawin; Petr Beier

doi:10.3762/bjoc.11.162

Pyridine-promoted dediazoniation of aryldiazonium tetrafluoroborates: application to the synthesis of SF₅-substituted phenylboronic esters and iodobenzenes

George Iakobson, Junyi Du, Alexandra Martha Zoya Slawin, Petr Beier^*

^*Corresponding author for this work

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

Abstract

Pyridine promotes dediazoniation of aryldiazonium tetrafluoroborates. The formed aryl radicals were trapped with B₂pin₂, iodine, or tetrahydrofuran to afford boronic esters, iodobenzenes and benzenes, respectively. The application to the synthesis of (pentafluorosulfanyl) phenylboronic esters, iodo(pentafluorosulfanyl)benzenes and (pentafluorosulfanyl)benzene is shown.

Original language	English
Pages (from-to)	1494-1502
Number of pages	9
Journal	Beilstein Journal of Organic Chemistry
Volume	11
DOIs	https://doi.org/10.3762/bjoc.11.162
Publication status	Published - 26 Aug 2015

Keywords

Borylation
Diazonium salts
Iodination
Pyridine
Sulfur pentafluorides

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10.3762/bjoc.11.162Licence: CC BY

Du_2015_SF5-subPhenylboronicEsters_JoOC_CC
© 2015 Iakobson et al; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Final published version, 366 KBLicence: CC BY

Pyridine-promoted dediazoniation of aryldiazonium tetrafluoroborates: application to the synthesis of SF5-substituted phenylboronic esters and iodobenzenes (dataset)
Iakobson, G. (Creator), Du, J. (Creator), Slawin, A. M. Z. (Creator) & Beier, P. (Creator), Cambridge Crystallographic Data Centre, 2015
https://dx.doi.org/10.5517/ccdc.csd.cc12wtrj and one more link, https://dx.doi.org/10.5517/ccdc.csd.cc12wtsk (show fewer)
Dataset

Cite this

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title = "Pyridine-promoted dediazoniation of aryldiazonium tetrafluoroborates: application to the synthesis of SF5-substituted phenylboronic esters and iodobenzenes",

abstract = "Pyridine promotes dediazoniation of aryldiazonium tetrafluoroborates. The formed aryl radicals were trapped with B2pin2, iodine, or tetrahydrofuran to afford boronic esters, iodobenzenes and benzenes, respectively. The application to the synthesis of (pentafluorosulfanyl) phenylboronic esters, iodo(pentafluorosulfanyl)benzenes and (pentafluorosulfanyl)benzene is shown.",

keywords = "Borylation, Diazonium salts, Iodination, Pyridine, Sulfur pentafluorides",

author = "George Iakobson and Junyi Du and Slawin, {Alexandra Martha Zoya} and Petr Beier",

note = "Financial support from the Academy of Sciences of the Czech Republic (Research Plan RVO: 61388963) and the Grant Agency of the Czech Republic (P207/12/0072) is gratefully acknowledged.",

year = "2015",

month = aug,

day = "26",

doi = "10.3762/bjoc.11.162",

language = "English",

volume = "11",

pages = "1494--1502",

journal = "Beilstein Journal of Organic Chemistry",

issn = "1860-5397",

publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

}

Pyridine-promoted dediazoniation of aryldiazonium tetrafluoroborates: application to the synthesis of SF₅-substituted phenylboronic esters and iodobenzenes. / Iakobson, George; Du, Junyi; Slawin, Alexandra Martha Zoya et al.
In: Beilstein Journal of Organic Chemistry, Vol. 11, 26.08.2015, p. 1494-1502.

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

TY - JOUR

T1 - Pyridine-promoted dediazoniation of aryldiazonium tetrafluoroborates

T2 - application to the synthesis of SF5-substituted phenylboronic esters and iodobenzenes

AU - Iakobson, George

AU - Du, Junyi

AU - Slawin, Alexandra Martha Zoya

AU - Beier, Petr

N1 - Financial support from the Academy of Sciences of the Czech Republic (Research Plan RVO: 61388963) and the Grant Agency of the Czech Republic (P207/12/0072) is gratefully acknowledged.

PY - 2015/8/26

Y1 - 2015/8/26

N2 - Pyridine promotes dediazoniation of aryldiazonium tetrafluoroborates. The formed aryl radicals were trapped with B2pin2, iodine, or tetrahydrofuran to afford boronic esters, iodobenzenes and benzenes, respectively. The application to the synthesis of (pentafluorosulfanyl) phenylboronic esters, iodo(pentafluorosulfanyl)benzenes and (pentafluorosulfanyl)benzene is shown.

AB - Pyridine promotes dediazoniation of aryldiazonium tetrafluoroborates. The formed aryl radicals were trapped with B2pin2, iodine, or tetrahydrofuran to afford boronic esters, iodobenzenes and benzenes, respectively. The application to the synthesis of (pentafluorosulfanyl) phenylboronic esters, iodo(pentafluorosulfanyl)benzenes and (pentafluorosulfanyl)benzene is shown.

KW - Borylation

KW - Diazonium salts

KW - Iodination

KW - Pyridine

KW - Sulfur pentafluorides

U2 - 10.3762/bjoc.11.162

DO - 10.3762/bjoc.11.162

M3 - Article

AN - SCOPUS:84962130140

SN - 1860-5397

VL - 11

SP - 1494

EP - 1502

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

Pyridine-promoted dediazoniation of aryldiazonium tetrafluoroborates: application to the synthesis of SF5-substituted phenylboronic esters and iodobenzenes

Abstract

Keywords

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Datasets

Pyridine-promoted dediazoniation of aryldiazonium tetrafluoroborates: application to the synthesis of SF5-substituted phenylboronic esters and iodobenzenes (dataset)

Cite this

Pyridine-promoted dediazoniation of aryldiazonium tetrafluoroborates: application to the synthesis of SF₅-substituted phenylboronic esters and iodobenzenes