Suzuki Coupling of Protected Aryl Diazonium Ions: Expanding the Knowledge of Triazabutadiene Compatible Reactions

Abigail J. Shepard; Julia A. Townsend; Christopher Foley; Christopher Hulme; Michael T. Marty; John C. Jewett

doi:10.1021/acs.orglett.1c00257

Suzuki Coupling of Protected Aryl Diazonium Ions: Expanding the Knowledge of Triazabutadiene Compatible Reactions

Abigail J. Shepard, Julia A. Townsend, Christopher Foley, Christopher Hulme, Michael T. Marty, John C. Jewett

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

4 Scopus citations

Abstract

Aryl diazonium ions are important in synthesis and chemical biology, and the acid-labile triazabutadiene can protect this handle for future use. We report a Suzuki coupling strategy that is compatible with the triazabutadiene scaffold, expanding the scope of synthetically available triazabutadienes. Shown herein, the triazabutadiene scaffold remains intact and reactive after coupling, as demonstrated by releasing the aryl diazonium ion to label a tyrosine-rich model protein.

Original language	English (US)
Pages (from-to)	1851-1855
Number of pages	5
Journal	Organic Letters
Volume	23
Issue number	5
DOIs	https://doi.org/10.1021/acs.orglett.1c00257
State	Published - Mar 5 2021

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.1c00257

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title = "Suzuki Coupling of Protected Aryl Diazonium Ions: Expanding the Knowledge of Triazabutadiene Compatible Reactions",

abstract = "Aryl diazonium ions are important in synthesis and chemical biology, and the acid-labile triazabutadiene can protect this handle for future use. We report a Suzuki coupling strategy that is compatible with the triazabutadiene scaffold, expanding the scope of synthetically available triazabutadienes. Shown herein, the triazabutadiene scaffold remains intact and reactive after coupling, as demonstrated by releasing the aryl diazonium ion to label a tyrosine-rich model protein.",

author = "Shepard, {Abigail J.} and Townsend, {Julia A.} and Christopher Foley and Christopher Hulme and Marty, {Michael T.} and Jewett, {John C.}",

note = "Publisher Copyright: {\textcopyright} ",

year = "2021",

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doi = "10.1021/acs.orglett.1c00257",

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T1 - Suzuki Coupling of Protected Aryl Diazonium Ions

T2 - Expanding the Knowledge of Triazabutadiene Compatible Reactions

AU - Shepard, Abigail J.

AU - Townsend, Julia A.

AU - Foley, Christopher

AU - Hulme, Christopher

AU - Marty, Michael T.

AU - Jewett, John C.

N1 - Publisher Copyright: ©

PY - 2021/3/5

Y1 - 2021/3/5

N2 - Aryl diazonium ions are important in synthesis and chemical biology, and the acid-labile triazabutadiene can protect this handle for future use. We report a Suzuki coupling strategy that is compatible with the triazabutadiene scaffold, expanding the scope of synthetically available triazabutadienes. Shown herein, the triazabutadiene scaffold remains intact and reactive after coupling, as demonstrated by releasing the aryl diazonium ion to label a tyrosine-rich model protein.

AB - Aryl diazonium ions are important in synthesis and chemical biology, and the acid-labile triazabutadiene can protect this handle for future use. We report a Suzuki coupling strategy that is compatible with the triazabutadiene scaffold, expanding the scope of synthetically available triazabutadienes. Shown herein, the triazabutadiene scaffold remains intact and reactive after coupling, as demonstrated by releasing the aryl diazonium ion to label a tyrosine-rich model protein.

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AN - SCOPUS:85101602011

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SP - 1851

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JO - Organic Letters

JF - Organic Letters

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ER -

Suzuki Coupling of Protected Aryl Diazonium Ions: Expanding the Knowledge of Triazabutadiene Compatible Reactions

Abstract

ASJC Scopus subject areas

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CCDC 2042943: Experimental Crystal Structure Determination

CCDC 2042945: Experimental Crystal Structure Determination

CCDC 2042946: Experimental Crystal Structure Determination

Cite this

Suzuki Coupling of Protected Aryl Diazonium Ions: Expanding the Knowledge of Triazabutadiene Compatible Reactions

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

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Datasets

CCDC 2042943: Experimental Crystal Structure Determination

CCDC 2042945: Experimental Crystal Structure Determination

CCDC 2042946: Experimental Crystal Structure Determination

Cite this