Rapid in Situ Generation of Benzene Diazonium Ions under Basic Aqueous Conditions from Bench-Stable Triazabutadienes

Jie He; Flora W. Kimani; John C. Jewett

doi:10.1055/s-0036-1588797

Rapid in Situ Generation of Benzene Diazonium Ions under Basic Aqueous Conditions from Bench-Stable Triazabutadienes

Jie He
, Flora W. Kimani
, John C. Jewett

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

9 Scopus citations

Abstract

Aryl diazonium ions are useful across a range of chemical/biochemical areas. These species are generally made using strongly acidic conditions, which can be detrimental to acid-sensitive functional groups. The ability to generate benzene diazonium ions under basic aqueous conditions is reported herein along with newfound understanding on the aqueous reactivity of solubilized triazabutadienes whereby π-interactions appear to confer a large degree of stability.

Original language	English (US)
Pages (from-to)	1767-1770
Number of pages	4
Journal	Synlett
Volume	28
Issue number	14
DOIs	https://doi.org/10.1055/s-0036-1588797
State	Published - Sep 1 2017

Keywords

acids
bioorganic chemistry
cleavage
diazonium ions
protecting groups

ASJC Scopus subject areas

Organic Chemistry

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10.1055/s-0036-1588797

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title = "Rapid in Situ Generation of Benzene Diazonium Ions under Basic Aqueous Conditions from Bench-Stable Triazabutadienes",

abstract = "Aryl diazonium ions are useful across a range of chemical/biochemical areas. These species are generally made using strongly acidic conditions, which can be detrimental to acid-sensitive functional groups. The ability to generate benzene diazonium ions under basic aqueous conditions is reported herein along with newfound understanding on the aqueous reactivity of solubilized triazabutadienes whereby π-interactions appear to confer a large degree of stability.",

keywords = "acids, bioorganic chemistry, cleavage, diazonium ions, protecting groups",

author = "Jie He and Kimani, \{Flora W.\} and Jewett, \{John C.\}",

note = "Publisher Copyright: {\textcopyright} 2017 Georg Thieme Verlag KG Stuttgart · New York.",

year = "2017",

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T1 - Rapid in Situ Generation of Benzene Diazonium Ions under Basic Aqueous Conditions from Bench-Stable Triazabutadienes

AU - He, Jie

AU - Kimani, Flora W.

AU - Jewett, John C.

PY - 2017/9/1

Y1 - 2017/9/1

N2 - Aryl diazonium ions are useful across a range of chemical/biochemical areas. These species are generally made using strongly acidic conditions, which can be detrimental to acid-sensitive functional groups. The ability to generate benzene diazonium ions under basic aqueous conditions is reported herein along with newfound understanding on the aqueous reactivity of solubilized triazabutadienes whereby π-interactions appear to confer a large degree of stability.

AB - Aryl diazonium ions are useful across a range of chemical/biochemical areas. These species are generally made using strongly acidic conditions, which can be detrimental to acid-sensitive functional groups. The ability to generate benzene diazonium ions under basic aqueous conditions is reported herein along with newfound understanding on the aqueous reactivity of solubilized triazabutadienes whereby π-interactions appear to confer a large degree of stability.

KW - acids

KW - bioorganic chemistry

KW - cleavage

KW - diazonium ions

KW - protecting groups

UR - https://www.scopus.com/pages/publications/85018409736

UR - https://www.scopus.com/pages/publications/85018409736#tab=citedBy

U2 - 10.1055/s-0036-1588797

DO - 10.1055/s-0036-1588797

M3 - Article

AN - SCOPUS:85018409736

SN - 0936-5214

VL - 28

SP - 1767

EP - 1770

JO - Synlett

JF - Synlett

IS - 14

ER -

Rapid in Situ Generation of Benzene Diazonium Ions under Basic Aqueous Conditions from Bench-Stable Triazabutadienes

Abstract

Keywords

ASJC Scopus subject areas

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