Photochemical Sonogashira coupling reactions: beyond traditional palladium–copper catalysis

Singh, Puja; Shaikh, Aslam C.

doi:10.1039/d3cc03855f

Cited by 9 publications

(4 citation statements)

References 122 publications

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“…[12] Furthermore, numerous seminal reactions employing 1-alkynylsilanes have been the subject of dedicated review articles. [221][222][223][224] Considering these factors, the author has selectively focused on a subset of recent advancements (2-3 examples of each), thus underlining the pivotal role of 1-silyl-1-alkynes in organic chemistry. It is important to note, however, that this treatment does not align with the comprehensive scope of a review article specifically dedicated to the applications of 1-alkynylsilanes.…”

Section: Selected Applications Of 1-alkynylsilanesmentioning

confidence: 99%

Synthesis of Alkynylsilanes: A Review of the State of the Art

Kuciński

2024

Adv Synth Catal

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This contribution offers a comprehensive overview of methods for forging sp C–Si bonds. Over time, alkynylsilanes (silylacetylenes), once considered mere byproducts of hydrosilylation processes, have become essential building blocks in organic synthesis. This literature review traces the evolution of their synthesis, from traditional methodologies relying on organolithium and organomagnesium compounds to more advanced cross‐coupling reactions involving hydro‐ and carbosilanes. Focused primarily on the past 25 years (2000‐2024), it also extensively references significant historical breakthroughs. By analyzing synthetic methodologies, the review not only offers a comprehensive survey of the current state of knowledge but also identifies areas for improvement. Furthermore, to emphasize the importance of 1‐alkynylsilanes (1‐silyl‐1‐alkynes), selected applications of these compounds are highlighted, confirming their significant potential in organic synthesis.

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Section: Selected Applications Of 1-alkynylsilanesmentioning

confidence: 99%

Synthesis of Alkynylsilanes: A Review of the State of the Art

Kuciński

2024

Adv Synth Catal

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“…This method is widely documented and recognized for its efficiency in constructing C–C bonds. 147–149 Iron oxide-based NPs were also explored for Sonogashira coupling reaction. 150 In this regard iron oxide based nanocatalyst, PdCu@GQD@Fe 3 O 4 , have been synthesized for the Sonogashira coupling reaction 151 which had been prepared by the modification of Fe 3 O 4 nanoparticles with graphene quantum dots (GQD) to stabilize the PdCu NPs (Fig.…”

Section: Catalytic Applications Of Nanosized Iron Oxidesmentioning

confidence: 99%

A review on sustainable iron oxide nanoparticles: syntheses and applications in organic catalysis and environmental remediation

Chaudhari,

Upadhyay,

Shinde

et al. 2024

Green Chem.

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“…Although palladium is a valuable metal due to its scarcity, it is widely used to get almost everywhere. − It is an essential part for catalytic converters in the automobiles . It is applied in the coupling reactions such as Heck, , Sonogashira, and Suzuki–Miyaura for the production of pharmaceuticals, fine chemicals, plastics, and high-tech materials in both industry and extensive research in academia. However, Pd-catalyzed reactions often generate products with Pd residue contamination even after purification.…”

Section: Introductionmentioning

confidence: 99%

Reaction-Based Multisignal Detection of Palladium with High Sensitivity, Selectivity, and Reliability

Mosleh,

Hardaker,

Bartolini

et al. 2024

ACS Appl. Opt. Mater.

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Due to vast application of palladium in academia and industry and its toxicity, it is critical to develop user-friendly, portable, and affordable methods for accurately detecting ultratrace Pd. In this study, a highly sensitive and selective fluorescent probe (N-butyl-4-alloxy-1,8-naphthalimide, compound 2) was synthesized, which demonstrated multiple signals [enhanced fluorescence (FL), ratiometric FL, and colorimetric responses] upon interaction with palladium. The compound 2 was designed by incorporating a naphthalimidebased fluorescent dye as the fluorophore and an allyl ether group as a responsive unit. Utilizing a Pd 0 -triggered cleavage reaction by a deallylation reaction through the Tsuji−Trost reaction, compound 2 exhibited rapid response, wide linearity, exceptional sensitivity with a limit of detection as low as 2.2 pM, and high selectivity toward palladium species. In addition, as a ratiometric and enhanced FL response, the probe could be developed as a portable sensor via naked eye visualization for semiquantitative and selective detection of palladium. Integrating with an easily available smartphone (with a camera and a color-analysis app), potential in situ quantitative detection was achieved at a low cost. The probe shows multiple signals for palladium detection and potential as a portable sensor, and this work provides valuable insights into developing sensors with good sensitivity, selectivity, improved reliability, and portability for detection of palladium and other analytes of interest.

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Photochemical Sonogashira coupling reactions: beyond traditional palladium–copper catalysis

Abstract: Sonogashira coupling is one of the Nobel reactions discovered in 1975 to form a C—C bond using palladium and copper as co-catalysts. By incorporating alkyne functionalities either in macro or...

Cited by 9 publications

References 122 publications

Synthesis of Alkynylsilanes: A Review of the State of the Art

Synthesis of Alkynylsilanes: A Review of the State of the Art

A review on sustainable iron oxide nanoparticles: syntheses and applications in organic catalysis and environmental remediation

Reaction-Based Multisignal Detection of Palladium with High Sensitivity, Selectivity, and Reliability

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