Metal-catalyzed one-pot synthesis of tetrazines directly from aliphatic nitriles and hydrazine

Jun Yang; Mark R. Karver; Weilong Li; Swagat Sahu; Neal K. Devaraj

doi:10.1002/anie.201201117

Metal-catalyzed one-pot synthesis of tetrazines directly from aliphatic nitriles and hydrazine

Jun Yang, Mark R. Karver, Weilong Li, Swagat Sahu, Neal K. Devaraj^*

^*Corresponding author for this work

Medicine, Endocrinology Division

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

191 Scopus citations

Abstract

Paving the way: The lack of convenient synthetic methods is a significant roadblock to the broader use of 1,2,4,5-tetrazines in bioorthogonal chemistry and functional materials. Lewis acid metal catalysts-most notably divalent nickel and zinc salts-are described to catalyze the one-pot synthesis of 1,2,4,5-tetrazines directly from aliphatic nitriles (see scheme).

Original language	English (US)
Pages (from-to)	5222-5225
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	51
Issue number	21
DOIs	https://doi.org/10.1002/anie.201201117
State	Published - May 21 2012

Keywords

bioorthogonal synthesis
cycloaddition
heterocycles
metal catalysis
tetrazines

ASJC Scopus subject areas

General Chemistry
Catalysis

Access to Document

10.1002/anie.201201117

Cite this

@article{7adb0978aa1c4896bc2470d33a8f8f21,

title = "Metal-catalyzed one-pot synthesis of tetrazines directly from aliphatic nitriles and hydrazine",

abstract = "Paving the way: The lack of convenient synthetic methods is a significant roadblock to the broader use of 1,2,4,5-tetrazines in bioorthogonal chemistry and functional materials. Lewis acid metal catalysts-most notably divalent nickel and zinc salts-are described to catalyze the one-pot synthesis of 1,2,4,5-tetrazines directly from aliphatic nitriles (see scheme).",

keywords = "bioorthogonal synthesis, cycloaddition, heterocycles, metal catalysis, tetrazines",

author = "Jun Yang and Karver, {Mark R.} and Weilong Li and Swagat Sahu and Devaraj, {Neal K.}",

year = "2012",

month = may,

day = "21",

doi = "10.1002/anie.201201117",

language = "English (US)",

volume = "51",

pages = "5222--5225",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "21",

}

TY - JOUR

T1 - Metal-catalyzed one-pot synthesis of tetrazines directly from aliphatic nitriles and hydrazine

AU - Yang, Jun

AU - Karver, Mark R.

AU - Li, Weilong

AU - Sahu, Swagat

AU - Devaraj, Neal K.

PY - 2012/5/21

Y1 - 2012/5/21

N2 - Paving the way: The lack of convenient synthetic methods is a significant roadblock to the broader use of 1,2,4,5-tetrazines in bioorthogonal chemistry and functional materials. Lewis acid metal catalysts-most notably divalent nickel and zinc salts-are described to catalyze the one-pot synthesis of 1,2,4,5-tetrazines directly from aliphatic nitriles (see scheme).

AB - Paving the way: The lack of convenient synthetic methods is a significant roadblock to the broader use of 1,2,4,5-tetrazines in bioorthogonal chemistry and functional materials. Lewis acid metal catalysts-most notably divalent nickel and zinc salts-are described to catalyze the one-pot synthesis of 1,2,4,5-tetrazines directly from aliphatic nitriles (see scheme).

KW - bioorthogonal synthesis

KW - cycloaddition

KW - heterocycles

KW - metal catalysis

KW - tetrazines

UR - http://www.scopus.com/inward/record.url?scp=84862098433&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84862098433&partnerID=8YFLogxK

U2 - 10.1002/anie.201201117

DO - 10.1002/anie.201201117

M3 - Article

C2 - 22511586

AN - SCOPUS:84862098433

SN - 1433-7851

VL - 51

SP - 5222

EP - 5225

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 21

ER -

Metal-catalyzed one-pot synthesis of tetrazines directly from aliphatic nitriles and hydrazine

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this