Efficient homologation of acetylenes to allenes

Crabbé, P.; Fillion, H.; André, Daniel; Luche, Jean‐Louis

doi:10.1039/c39790000859

Cited by 166 publications

(58 citation statements)

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“…[8][9][10][11][12][13] However, these reports have only addressed a limited range of acetylene systems. In addition, effects of the nature of aryl substituents as well as variation of the catalyst component on the pattern of product and yield distribution have to date not been investigated.…”

Section: Introductionmentioning

confidence: 99%

Effect of Varying the Anionic Component of a Copper(I) Catalyst on Homologation of Arylacetylenes to Allenes by the Mannich Reaction

2007

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The effect of varying the anionic component of a copper(I) catalyst in the homologation of terminal arylacetylenes to allenes by the Mannich reaction was investigated. Varying amounts of allenes, Mannich bases and dimers were obtained depending on the nature of the anionic component of the copper catalyst. On the other hand, Eglinton–Glaser dimerizations were achieved in high yields with 0.5 equiv. of triethylamine. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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Section: Introductionmentioning

confidence: 99%

Effect of Varying the Anionic Component of a Copper(I) Catalyst on Homologation of Arylacetylenes to Allenes by the Mannich Reaction

2007

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“…Of special interest are catalytic processes, which directly build the three-carbon allene core by coupling two different fragments, thus allowing for convergent synthesis. The first of such processes was discovered in 1979, namely the Crabbé homologation[4] (Figure 1a). This is a CuBr mediated three-component reaction between a terminal alkyne, formaldehyde, and diisopropylamine.…”

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confidence: 99%

A Cationic Gold(I) Complex as a General Catalyst for the Intermolecular Hydroamination of Alkynes: Application to the One‐Pot Synthesis of Allenes from Two Alkynes and a Sacrificial Amine

Zeng¹,

Frey²,

Kousar³

et al. 2009

Chemistry A European J

139

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The evolution of the structural and optical characteristics of polymorphic organic perylene nanoparticles (NPs) is demonstrated by controlling the π–π interactions using a hydrothermal process. The light‐emission colors of the perylene NPs vary gradually from yellow to green to light blue with increasing hydrothermal temperature from 110 to 160 °C. An enhanced crystallinity of the NPs from 110 °C to a critical temperature Tc of 140 °C and a transition to the amorphous phase above Tc are observed. The evolution of the photo‐luminescence (PL) and optical‐absorption characteristics in terms of variations in the crystallinity and physical dimensions (size and shape) of the perylene NPs resulting from the hydrothermal process are analyzed. These results are confirmed by nanoscale PL measurements for single NPs using laser confocal microscopy. The photovoltaic characteristics of organic solar cells (OSCs) are improved through the use of the perylene NPs. It is found that the performance of the OSCs is strongly correlated with the optical‐absorption properties of the perylene NPs.

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“…The uridine allene 9 was readily prepared from uridine, 2',3',5'-triacetate via Npropargylation followed by homologation of the terminal alkyne using a cuprous bromide-catalysed reaction 16 with formaldehyde and diisopropylamine (DIPA) via a giving the uridine allene 9 in 55% yield (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

γ-Carboline AC190 analogues via palladium catalysed allene insertion stereo and regioselective 3- and 5-component cascades

et al. 2016

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Efficient homologation of acetylenes to allenes

Cited by 166 publications

References 0 publications

Effect of Varying the Anionic Component of a Copper(I) Catalyst on Homologation of Arylacetylenes to Allenes by the Mannich Reaction

Effect of Varying the Anionic Component of a Copper(I) Catalyst on Homologation of Arylacetylenes to Allenes by the Mannich Reaction

A Cationic Gold(I) Complex as a General Catalyst for the Intermolecular Hydroamination of Alkynes: Application to the One‐Pot Synthesis of Allenes from Two Alkynes and a Sacrificial Amine

γ-Carboline AC190 analogues via palladium catalysed allene insertion stereo and regioselective 3- and 5-component cascades

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