Tetraalkynylstannanes in the Stille cross coupling reaction: a new effective approach to arylalkynes

Levashov, A. S.; Buryi, D. S.; Гончарова, О. В.; Коншин, В. В.; Dotsenko, V. V.; Andreev, A. A.

doi:10.1039/c6nj03905g

Cited by 23 publications

(8 citation statements)

References 32 publications

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“…According to our postulations, the first step involves the reaction of CuI with 1 H -benzotriazole to give intermediate A . 10,11 When this intermediate A reacts with terminal alkyne, it activates the sp C–H proton of the alkyne, which further can be easily removed by the use of a base (e.g., K 2 CO 3 ) and afforded the coordination adduct intermediate B . This intermediate at the last step undergoes C–C bond formation via intermediates C and D to give the respective conjugated 1,3-dialkynes as the final coupling product 2 .…”

Section: Resultsmentioning

confidence: 99%

Benzotriazole as an Efficient Ligand in Cu-Catalyzed Glaser Reaction

Singh

Mishra

et al. 2019

ACS Omega

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Benzotriazole has been established as an efficient ligand in Cu-catalyzed cross-coupling of terminal alkynes to form 1,3-dialkynes using CuI as the catalyst and K 2 CO 3 as the base at room temperature in an open round-bottom flask. The established protocol has the following notable advantages: simple to handle, easy work-up, mild reaction condition, high substrate scope, requirement of less quantity of ligand and also Cu-catalyst, less expensive, and high reaction yield.

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Section: Resultsmentioning

confidence: 99%

Benzotriazole as an Efficient Ligand in Cu-Catalyzed Glaser Reaction

Singh

Mishra

et al. 2019

ACS Omega

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“…This reaction involves coupling between aryl stanners species with organic electrophiles such as aryl halide in the presence of palladium, Pd (0), as a catalyst (Scheme 11) [91,92]. The success and widespread use of this reaction is attributed to the mild reagents of organotin, which are well matched with a diverse number of functional groups [93,94]. Moreover, organostanners are insensitive to moisture and oxygen, allowing stille reactions to be undemanding and performed under relatively neutral conditions [93,94].…”

Section: Stille Cross-coupling Reactionmentioning

confidence: 99%

“…The success and widespread use of this reaction is attributed to the mild reagents of organotin, which are well matched with a diverse number of functional groups [93,94]. Moreover, organostanners are insensitive to moisture and oxygen, allowing stille reactions to be undemanding and performed under relatively neutral conditions [93,94]. As good as this reaction is, the drawback lies with the contamination and toxic waste products as a result of the use of organotin compounds such as Bu 3 SnR [95][96][97].…”

Section: Stille Cross-coupling Reactionmentioning

confidence: 99%

π-Conjugated Polymers and Their Application in Organic and Hybrid Organic-Silicon Solar Cells

et al. 2022

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The evolution and emergence of organic solar cells and hybrid organic-silicon heterojunction solar cells have been deemed as promising sustainable future technologies, owing to the use of π-conjugated polymers. In this regard, the scope of this review article presents a comprehensive summary of the applications of π-conjugated polymers as hole transporting layers (HTLs) or emitters in both organic solar cells and organic-silicon hybrid heterojunction solar cells. The different techniques used to synthesize these polymers are discussed in detail, including their electronic band structure and doping mechanisms. The general architecture and principle of operating heterojunction solar cells is addressed. In both discussed solar cell types, incorporation of π-conjugated polymers as HTLs have seen a dramatic increase in efficiencies attained by these devices, owing to the high transmittance in the visible to near-infrared region, reduced carrier recombination, high conductivity, and high hole mobilities possessed by the p-type polymeric materials. However, these cells suffer from long-term stability due to photo-oxidation and parasitic absorptions at the anode interface that results in total degradation of the polymeric p-type materials. Although great progress has been seen in the incorporation of conjugated polymers in the various solar cell types, there is still a long way to go for cells incorporating polymeric materials to realize commercialization and large-scale industrial production due to the shortcomings in the stability of the polymers. This review therefore discusses the progress in using polymeric materials as HTLs in organic solar cells and hybrid organic-silicon heterojunction solar cells with the intention to provide insight on the quest of producing highly efficient but less expensive solar cells.

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“…These drawbacks can be avoided with the replacement of monoalkynylstannanes with tetraalkynyltin reagents, as they are far less toxic and the molecular weight of the tin residue is significantly lower in comparison with trialkyltin reagents. Recently, we reported the Stille-type coupling reaction of tetraalkynylstannanes with aryl halides leading to aryl acetylenes and SnHal4 [12] and aldehydes leading to alkynyl ketones [13,14]. Earlier, we developed convenient methods for preparation of tetraalkinyltin species from either SnCl4 [15] or tin tetra(N,N-diethylcarbamate) [16].…”

Section: Introductionmentioning

confidence: 99%