Synthesis of Di‐Substituted Alkynes <i>via</i> Palladium‐Catalyzed Decarboxylative Coupling and C‐H Activation

Gómez‐Herrera, Alberto; Nahra, Fady; Wu, Jiufeng; Izquierdo, Frédéric; Brill, Marcel; Cazin, Catherine S. J.; Nolan, Steven P.

doi:10.1002/slct.201803805

Cited by 13 publications

(6 citation statements)

References 52 publications

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“…In addition, the Lee group reported decarboxylative C(sp 2 )−H arylation of electron-deficient azoles using the Pd(0)−NHC complex (not shown). 137,138 This approach offers an alternative strategy to the direct C(sp 2 )−H arylation of heterocycles using Pd−NHC catalysts.…”

Section: Palladium−nhc Complexesmentioning

confidence: 99%

N-Heterocyclic Carbene Complexes in C–H Activation Reactions

et al. 2020

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In this contribution, we provide a comprehensive overview of C−H activation methods promoted by NHC−transition metal complexes, covering the literature since 2002 (the year of the first report on metal−NHC-catalyzed C−H activation) through June 2019, focusing on both NHC ligands and C−H activation methods. This review covers C−H activation reactions catalyzed by group 8 to 11 NHC−metal complexes. Through discussing the role of NHC ligands in promoting challenging C−H activation methods, the reader is provided with an overview of this important area and its crucial role in forging carbon−carbon and carbon−heteroatom bonds by directly engaging ubiquitous C−H bonds.

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Section: Palladium−nhc Complexesmentioning

confidence: 99%

N-Heterocyclic Carbene Complexes in C–H Activation Reactions

et al. 2020

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“…[ 138 ] Nolan described a decarboxylative cross‐coupling of aryl bromide and phenylpropiolic acid using [Pd(η 3 ‐cin)Cl(IPr)] pre‐catalyst. [ 139 ] Substrates containing C(sp 2 )‐Br bonds, such as bromofluoroalkenes, were successfully used for stereoselective synthesis of fluoroenynes.…”

Section: Sonogashira‐related Coupling Reactionsmentioning

confidence: 99%

Recent Expedition inPd‐CatalyzedSonogashira Coupling and Related Processes^†

2023

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Sonogashira cross-coupling protocol, typically showing the reaction between aryl/vinyl halide and terminal alkyne, has been a widely used protocol for constructing C(sp 2 )-C(sp) bond. The resulting internal alkynes are highly versatile for reaching differently functionalized alkyne-containing scaffolds or serving as valuable synthetic synthons to many other functional groups. It is worth noting that products originated from this coupling reaction are mostly applicable to be transformed into corresponding Z-alkene, alkane, or heterocyclic moieties in natural product syntheses. The reaction conditions and catalyst systems are able to be tweaked in order to facilitate the activation of steric hindered and/or electron-rich electrophiles. Pd-catalyzed copper-free Sonogashira coupling reaction has caught increasing attention as the improved method can be more environmentally friendly. What is more, the conditions of the coupling reaction can be readily amended to allow the fusion of other carbonylation or decarboxylation step in the catalytic cycle, and thus allow more complex yet versatile convergent synthesis to proceed in an operationally simple one-pot manner.

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“…4,129.8,128.5,128.3,128.1,125.3,123.1,122.2,88.8,. Colorless oil, 23 yield 148 mg (89%) R f = 0.3 (2% ethyl acetate/n-hexane); 1 H NMR (500 MHz, CDCl 3 ): δ 7.39 −7.38 (m, 2H), 7.29−7.28 (m, 3H), 2.57 (t, J = 6.5 Hz, 2H), 2.54−2.51 (m, 2H), 1.96−1.90 (m, 2H); 13 C { 1 H} NMR (125 MHz, CDCl 3 ): δ 131. 6, 128.7, 128.4, 128.1, 123.3, 119.3, 87.0, 82.4, 24.7, 18.6, and 16.2 ppm. (3-Cyclohexylprop-1-yn-1-yl)benzene (7l).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Glycosyl Triazole Ligand for Temperature-Dependent Competitive Reactions of Cu-Catalyzed Sonogashira Coupling and Glaser Coupling

Mishra

Singh

et al. 2021

J. Org. Chem.

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Glycosyl triazoles have been introduced as efficient ligands for the Cu-catalyzed Sonogashira reaction to overcome the challenges of sideways homocoupling reactions in Cu catalysis in this reaction. The atmospheric oxygen in a sealed tube did not affect the coupling, and no need of complete exclusion of oxygen was experienced in the presence of glycohybrid triazole ligand L3. High product yields were obtained at 130 °C for a variety of substrates including aliphatic and aromatic terminal alkynes and differently substituted aromatic halides including 9-bromo noscapine. In contrast, at room temperature, a very low loading of the L3-Cu catalytic system could produce excellent yields in Glaser coupling including homocoupling and heterocoupling of a variety of aliphatic and aromatic alkynes.

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Synthesis of Di‐Substituted Alkynes via Palladium‐Catalyzed Decarboxylative Coupling and C‐H Activation

Cited by 13 publications

References 52 publications

N-Heterocyclic Carbene Complexes in C–H Activation Reactions

N-Heterocyclic Carbene Complexes in C–H Activation Reactions

Recent Expedition inPd‐CatalyzedSonogashira Coupling and Related Processes^†

Glycosyl Triazole Ligand for Temperature-Dependent Competitive Reactions of Cu-Catalyzed Sonogashira Coupling and Glaser Coupling

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Synthesis of Di‐Substituted Alkynes via Palladium‐Catalyzed Decarboxylative Coupling and C‐H Activation

Cited by 13 publications

References 52 publications

N-Heterocyclic Carbene Complexes in C–H Activation Reactions

N-Heterocyclic Carbene Complexes in C–H Activation Reactions

Recent Expedition inPd‐CatalyzedSonogashira Coupling and Related Processes†

Glycosyl Triazole Ligand for Temperature-Dependent Competitive Reactions of Cu-Catalyzed Sonogashira Coupling and Glaser Coupling

Contact Info

Product

Resources

About

Recent Expedition inPd‐CatalyzedSonogashira Coupling and Related Processes^†