N‐Heterocyclic Carbene Iron(III) Porphyrin‐Catalyzed Intramolecular C(sp<sup>3</sup>)–H Amination of Alkyl Azides

Shing, Ka-Pan; Liu, Yungen; Cao, Bei; Chang, Xiaoyong; You, Tingjie; Che, Chi‐Ming

doi:10.1002/ange.201806059

Cited by 27 publications

(9 citation statements)

References 33 publications

(17 reference statements)

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“… 52 The group of Che used an NHC-PorFe catalyst for the preparation of saturated nitrogen heterocycles from alkyl azides. 53 Recently, a highly functional group tolerant PcMn analogue was disclosed for intermolecular, benzylic C–H amination; multiple late-stage derivatizations of biologically active compounds were exemplified ( Scheme 3 A). 54 In parallel, the group of Zhang has led the development of the corresponding PorCo systems.…”

Section: Next Generation Metal Catalystsmentioning

confidence: 99%

C–H Activation: Toward Sustainability and Applications

2021

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Since the definition of the “12 Principles of Green Chemistry” more than 20 years ago, chemists have become increasingly mindful of the need to conserve natural resources and protect the environment through the judicious choice of synthetic routes and materials. The direct activation and functionalization of C–H bonds, bypassing intermediate functional group installation is, in abstracto , step and atom economic, but numerous factors still hinder the sustainability of large-scale applications. In this Outlook, we highlight the research areas seeking to overcome the sustainability challenges of C–H activation: the pursuit of abundant metal catalysts, the avoidance of static directing groups, the replacement of metal oxidants, and the introduction of bioderived solvents. We close by examining the progress made in the subfield of aryl C–H borylation from its origins, through highly efficient but precious Ir-based systems, to emerging 3d metal catalysts. The future growth of this field will depend on industrial uptake, and thus we urge researchers to strive toward sustainable C–H activation.

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Section: Next Generation Metal Catalystsmentioning

confidence: 99%

C–H Activation: Toward Sustainability and Applications

2021

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“…[41][42][43][44][45][46][47][48][49][50][51][52][53] Recently, we discovered dioxazolones can undergo intermolecular N-N coupling with arylamines to make hydrazides under either iridium or iron catalysis. [54][55][56][57][58][59][60][61][62][63][64] Mechanistic studies of the Ir-catalyzed system indicated an outer-sphere nucleophilic attack of the nitrogen group of Ir-nitrenoid intermediate by amine leads to the N-N coupling product.…”

Section: Resultsmentioning

confidence: 99%

Nitrene-Mediated P–N Coupling Under Iron Catalysis

et al. 2022

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P-N and P=N bonds play important roles in the design and synthesis of functional molecules such as bioactive compounds and organic ligands for catalysis. Existing methods for P-N coupling mostly rely on Staudinger condensation or nucleophilic substitution between phosphorus electrophiles and amine nucleophiles. Herein, we report a nitrene-mediated intermolecular P-N coupling reaction between various phosphorus nucleophiles and dioxazolones under simple iron-catalyzed conditions. These reactions offer an efficient, versatile, and broadly applicable method for synthesis of a range of N-P compounds including amidophosphines, iminophosphonamides, phosphinamides, aminophosphines, and iminophosphoranes from readily available precursors under mild conditions.

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“…Our synthesis ( Scheme 4 ) began with the preparation of 2-bromo-5-(but-1-en-1-yl)pyridine ( 4 ) from commercially available 6-bromonicotinaldehyde ( 5 ) and n -propyltriphenyl-phosphonium bromide by using the Wittig reaction [ 30 ], followed by a hydrogenation reaction [ 31 ] to afford 2-bromo-5-butylpyridine ( 3 ). Once 2-bromo-5-butylpyridine ( 3 ) was in hand, a carbonylation reaction [ 32 ] was carried out immediately and methyl 5-butylpicolinate ( 2 ) was obtained.…”

Section: Resultsmentioning

confidence: 99%

Concise Total Synthesis and Antifungal Activities of Fusaric Acid, a Natural Product

et al. 2020

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The total synthesis of a natural product alkaloid fusaric acid (FA), which exhibits herbicide, fungicide, insecticide and even diverse notable pharmacological activities, was accomplished in four steps using commercially available materials. The synthesis, based on a unified and flexible strategy using 6-bromonicotinaldehyde as a common intermediate, is concise, convergent, practical and can be carried out on a two-gram scale. This approach could be readily applicable to the synthesis of its analogues. In addition, FA had a wide range of inhibitory activities against 14 plant pathogenic fungi in this study, which demonstrated that as a leading compound, and it has great potential to be further developed as an agricultural fungicide.

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N‐Heterocyclic Carbene Iron(III) Porphyrin‐Catalyzed Intramolecular C(sp³)–H Amination of Alkyl Azides

Abstract: Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.

Cited by 27 publications

References 33 publications

C–H Activation: Toward Sustainability and Applications

C–H Activation: Toward Sustainability and Applications

Nitrene-Mediated P–N Coupling Under Iron Catalysis

Concise Total Synthesis and Antifungal Activities of Fusaric Acid, a Natural Product

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N‐Heterocyclic Carbene Iron(III) Porphyrin‐Catalyzed Intramolecular C(sp3)–H Amination of Alkyl Azides

Abstract: Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.

Cited by 27 publications

References 33 publications

C–H Activation: Toward Sustainability and Applications

C–H Activation: Toward Sustainability and Applications

Nitrene-Mediated P–N Coupling Under Iron Catalysis

Concise Total Synthesis and Antifungal Activities of Fusaric Acid, a Natural Product

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N‐Heterocyclic Carbene Iron(III) Porphyrin‐Catalyzed Intramolecular C(sp³)–H Amination of Alkyl Azides