Metal‐Catalyzed One‐Pot Synthesis of Tetrazines Directly from Aliphatic Nitriles and Hydrazine

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

doi:10.1002/anie.201201117

Cited by 219 publications

(165 citation statements)

References 63 publications

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“…Besides, they serve as common building blocks for high performance materials, polymers and molecular electronics [2][3][4] . In organic chemistry, nitriles serve as essential intermediates for the production of a variety of heterocycles 5,6 , as well as precursors for amines, amides, aldehydes and different carboxylic acid derivatives 7,8 . For their synthesis, commonly highly toxic HCN or metal cyanides (for example, HCN: TD Lo ¼ 0.055 mg kg À 1 (human, intravenous); KCN: LD 50 ¼ 5-10 mg kg À 1 (oral in rats, mice, rabbits); Zn(CN) 2 : LD 50 ¼ 54 mg kg À 1 (oral in rats)) have to be applied for nucleophilic substitutions of alkyl and aryl halides 9,10 or the classic Sandmeyer reaction 11 .…”

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confidence: 99%

Green synthesis of nitriles using non-noble metal oxides-based nanocatalysts

2014

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(Hetero)aromatic and aliphatic nitriles constitute major building blocks for organic synthesis and represent a versatile motif found in numerous medicinally and biologically important compounds. In general, these nitriles are synthesized by traditional cyanation procedures using toxic cyanides. With respect to green chemistry, the development of more sustainable and cost-efficient processes for the synthesis of advanced nitriles is highly desired. Here we report an environmentally benign synthesis of all kinds of structurally diverse aryl, heterocyclic, allylic and aliphatic nitriles from easily available alcohols applying aqueous ammonia and molecular oxygen. Key to success for this synthesis is the use of nitrogen-doped graphene-layered non-noble metal oxides as stable and durable nanocatalysts. As an example a renewable synthesis of adiponitrile, an industrially important bulk chemical is presented.

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confidence: 99%

Green synthesis of nitriles using non-noble metal oxides-based nanocatalysts

2014

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“…3-Methyl-6-phenyl-1,2,4,5-tetrazine 1, 25 naphthalimide dye 9, 26 and dichlorotetrazine 27 were prepared according to literature procedures. All other reagents and solvents were of commercial grade.…”

Section: Methodsmentioning

confidence: 99%

Regioselective inverse Diels-Alder reaction of unsymmetrical tetrazines with aldehydes and ketones

Adogla¹,

Xu²,

Li³

et al. 2015

Arkivoc

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“…Despite the potential power of the TCO/Tz reaction, difficulty in synthesizing Tz had hindered widespread application. This problem was recently addressed though with the report of a series of 1,2,4,5-Tzs by metal salt-catalyzed formation from nitriles [32] .…”

Section: History Of Developmentmentioning

confidence: 99%

Bioorthogonal chemistries for nanomaterial conjugation and targeting

Rahim

Kota

Lee

et al. 2013

Nanotechnology Reviews

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Bioorthogonal chemistries are covalent reaction pairs that proceed in the presence of biological components with complete specificity. A suite of reactions has been described to date that provides scientists and engineers with diverse operational characteristics for different applications. Nanomaterials in particular have benefitted from these new capabilities, resulting in improved coupling efficiencies and multifunctionality. In this review, we will discuss the application of bioorthogonal chemistries to different nanomaterial systems, highlighting the advantages and limitations for use in bioconjugation. We will also describe how recent improvements in the reaction speed of catalyst-free bioorthogonal chemistries have enabled the successful coupling of nanomaterials directly to live cells. Using a recently developed reaction pair, tetrazine and trans -cyclooctene, the direct covalent coupling to cells has been shown to occur on time-scales that are relevant for biological studies and diagnostic applications and can even amplify nanomaterial binding greater than tenfold relative to traditional immunoconjugates. This powerful technique still maintains exquisite specificity, however, yielding robust results in clinical diagnostic applications using human tissue and blood samples. Future work will likely focus on further advancement of the in situ amplification technique, such as increasing nanomaterial binding, enabling multiplexed detection through the use of orthogonal reaction systems and extension to applications in vivo .

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Metal‐Catalyzed One‐Pot Synthesis of Tetrazines Directly from Aliphatic Nitriles and Hydrazine

Cited by 219 publications

References 63 publications

Green synthesis of nitriles using non-noble metal oxides-based nanocatalysts

Green synthesis of nitriles using non-noble metal oxides-based nanocatalysts

Regioselective inverse Diels-Alder reaction of unsymmetrical tetrazines with aldehydes and ketones

Bioorthogonal chemistries for nanomaterial conjugation and targeting

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