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            ‐Butyl azidoformate

Carpino, Louis A.; Carpino, Barbara A.; Crowley, Paul J.; Giza, Chester A.; Terry, Paul H.

doi:10.1002/0471264180.os044.06

Cited by 4 publications

(8 citation statements)

References 11 publications

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“…50 The cycloaddition reaction is performed under relatively mild conditions starting from pristine MWCNTs and the freshly prepared tert-butyl azidoformate. 41 The tert-butyloxycarbonylaziridino-MWCNT (MW@N BOC ) intermediate undergoes 51 a thermal treatment under ultrahigh vacuum that readily and selectively decomposes the carbamate units into isobutene and CO 2 and leads to the target aziridine-NH-functionalized sample (MW@N Az ) (Scheme 1). 50 At odds with other covalent functionalization protocols where basic N-containing groups can be grafted to the surface of complex carbon structures as dangling arms, 11,12 the [2 + 1] nitrene cycloaddition guarantees a more intimate connection between the exohedral N-dopant and the sp 2 carbon network.…”

Section: Resultsmentioning

confidence: 99%

“…The adopted procedure for the N-decoration is based on a two-step protocol that includes a nitrene [2 + 1] cycloaddition to the π-electron system of MWCNTs − followed by a controlled thermal decomposition of the reaction product . The cycloaddition reaction is performed under relatively mild conditions starting from pristine MWCNTs and the freshly prepared tert -butyl azidoformate . The tert -butyloxycarbonylaziridino-MWCNT ( MW@N BOC ) intermediate undergoes a thermal treatment under ultrahigh vacuum that readily and selectively decomposes the carbamate units into isobutene and CO 2 and leads to the target aziridine-NH-functionalized sample ( MW@N Az ) (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

“…MKBH5814 V) and used as received. tert -Butyl azidoformate was prepared on a multigram scale according to literature procedures . Unless stated otherwise, all other chemicals were purchased from commercial suppliers and used as received without further purification.…”

Section: Methodsmentioning

confidence: 99%

See 2 more Smart Citations

Aziridine-Functionalized Multiwalled Carbon Nanotubes: Robust and Versatile Catalysts for the Oxygen Reduction Reaction and Knoevenagel Condensation

Tuci

Luconi

Rossin

et al. 2016

ACS Appl. Mater. Interfaces

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This paper describes the exohedral N-decoration of multiwalled carbon nanotubes (MWCNTs) with NH-aziridine groups via [2 + 1] cycloaddition of a tert-butyl-oxycarbonyl nitrene followed by controlled thermal decomposition of the cyclization product. The chemical grafting with N-containing groups deeply modifies the properties of the starting MWCNTs, generating new surface microenvironments with specific base (Brønsted) and electronic properties. Both of these features translate into a highly versatile single-phase heterogeneous catalyst (MW@N) with remarkable chemical and electrochemical performance. Its surface base character promotes the Knoevenagel condensation with activity superior to that of related state of the art N-doped and N-decorated carbon nanomaterials; the N-induced electronic surface redistribution drives the generation of high-energy surface "C" sites suitable for O activation and its subsequent electrochemical reduction (ORR).

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Aziridine-Functionalized Multiwalled Carbon Nanotubes: Robust and Versatile Catalysts for the Oxygen Reduction Reaction and Knoevenagel Condensation

Tuci

Luconi

Rossin

et al. 2016

ACS Appl. Mater. Interfaces

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“…The addition of alkali salts (one equiv.) had a positive effect on the conversion with K 3 PO 4 being superior to other potassium salts (entries [8][9][10]. While an increase of the BocN 3 equivalents had no effect on the conver-sion (entry 11), it was shown that the reaction could be promoted even with 0.5 equiv.…”

mentioning

confidence: 99%

“…BocN 3 , which is known to be a potential explosive, was employed in crude form without prior distillation. [9,10] Under identical conditions, 3-pyridin-2-ylthiophenes were subjected to the amination reaction. If the 2-position was available for C À H activation a facile amination was observed, which delivered the Boc-protected 2-aminothiophenes 3a and 3b in high yields ( Figure 1).…”

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confidence: 99%

Rhodium‐Catalyzed N‐tert‐Butoxycarbonyl (Boc) Amination by Directed CH Bond Activation

2016

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N-tert-Butoxycarbonyl azide (BocN 3 ) was shown to be an efficient and economic source for the directed introduction of N-Boc protected amino groups into the thiophene and benzene nucleus. Yields for the amination of 2-pyridin-2-ylthiophenes (10 examples) were 52-88%. For the amination of the respective benzenes (10 examples) yields between 54% and 99% were recorded with an improved reactivity observed for substrates that bear an electron-withdrawing group. The reaction was applied to short total syntheses of the indoloquinoline alkaloids quindoline and cryptolepine. The facile removal of the Boc protecting group was the key to the success of the syntheses. The scope of the reaction was extended to a C(sp 3 ) À H bond amination and to the amination of 2-phenyloxazoline. For the amination of 2-pyridin-2-ylbenzene a kinetic deuterium isotope effect of 2.0 was determined.

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Unraveling Surface Basicity and Bulk Morphology Relationship on Covalent Triazine Frameworks with Unique Catalytic and Gas Adsorption Properties

Tuci

Pilaski

et al. 2017

Adv Funct Materials

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This paper describes the exohedral N-decoration of multi-walled carbon nanotubes (MWCNTs) with NH-aziridine groups via [2+1] cycloaddition of a tert-butyl-oxycarbonyl nitrene followed by controlled thermal decomposition of the cyclization product. The chemical grafting with Ncontaining groups deeply modifies the properties of the starting MWCNTs, generating new surface microenvironments with specific base (Brønsted) and electronic properties. Both these features translate into a highly versatile single-phase heterogeneous catalyst (MW@N Az ) with remarkable chemical and electrochemical performance. Its surface base character promotes the Knoevenagel condensation with superior activity to that of related N-doped and N-decorated carbon nanomaterials of the state-of-the-art; the N-induced electronic surface redistribution drives the generation of high energy surface "C" sites suitable for O2 activation and its subsequent electrochemical reduction (ORR).

show abstract

t ‐Butyl azidoformate

Abstract: t ‐Butyl azidoformate product: t ‐Butyl azidoformate

Cited by 4 publications

References 11 publications

Aziridine-Functionalized Multiwalled Carbon Nanotubes: Robust and Versatile Catalysts for the Oxygen Reduction Reaction and Knoevenagel Condensation

Aziridine-Functionalized Multiwalled Carbon Nanotubes: Robust and Versatile Catalysts for the Oxygen Reduction Reaction and Knoevenagel Condensation

Rhodium‐Catalyzed N‐tert‐Butoxycarbonyl (Boc) Amination by Directed CH Bond Activation

Unraveling Surface Basicity and Bulk Morphology Relationship on Covalent Triazine Frameworks with Unique Catalytic and Gas Adsorption Properties

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