The Synthesis of Tetrasubstituted Cycloalkenes Bearing π‐Conjugated Substituents and Their Optical Properties

Čubiňák, Marek; Bigeon, John; Galář, Pavel; Ondič, Lukáš; Tobrman, Tomáš

doi:10.1002/slct.202103122

Cited by 3 publications

(3 citation statements)

References 53 publications

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“…A similar approach has been employed for the preparation of 2-substituted cyclobutanones [ 82 ] and cyclobutenones [ 83 ]. Further studies have shown that aluminum chloride facilitates the Negishi reaction of cycloalkenyl diphenyl phosphates at room temperature [ 84 , 85 ].…”

Section: Organophosphates As Electrophiles In Transition-metal-cataly...mentioning

confidence: 99%

Organophosphates as Versatile Substrates in Organic Synthesis

Oeser,

Tobrman

2024

Molecules

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This review summarizes the applications of organophosphates in organic synthesis. After a brief introduction, it discusses cross-coupling reactions, including both transition-metal-catalyzed and transition-metal-free substitution reactions. Subsequently, oxidation and reduction reactions are described. In addition, this review highlights the applications of organophosphates in the synthesis of natural compounds, demonstrating their versatility and importance in modern synthetic chemistry.

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Section: Organophosphates As Electrophiles In Transition-metal-cataly...mentioning

confidence: 99%

Organophosphates as Versatile Substrates in Organic Synthesis

Oeser,

Tobrman

2024

Molecules

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“…Tetrasubstituted alkenes, bearing a tetrasubstituted CC core, are widely used in material science, biomedicine, and chemistry . They also serve as useful chemical motifs for the synthesis of functional compounds . In particular, tetraphenylethylene (TPE), tetravinylethylene (TVE), tetraethynylethylene (TEE), and their derivatives have attracted much attention in the past several decades.…”

Section: Introductionmentioning

confidence: 99%

Unlocking Diverse π-Bond Enrichment Frameworks by the Synthesis and Conversion of Boronated Phenyldiethynylethylenes

Xie,

Li,

et al. 2024

J. Am. Chem. Soc.

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The π-bond enrichment frameworks not only serve as a crucial building block in organic synthesis but also assume a pivotal role in the fields of materials science, biomedicine, photochemistry, and other related disciplines owing to their distinctive structural characteristics. The incorporation of various substituents into the C�C double bonds of tetrasubstituted alkenes is currently a highly significant research area. However, the synthesis of tetrasubstituted alkenes with diverse substituents on double bonds poses a significant challenge in achieving stereoselectivity. Here, we reported an efficient and convergent route of Cu-catalyzed borylalkynylation of both symmetrical and unsymmetrical 1,3-diynes, B 2 pin 2 , and acetylene bromide to the construction of boronated phenyldiethynylethylene (BPDEE) derivatives with excellent chemo-, stereo-, and regioselectivities. BPDEE derivatives could transform into novel tetrasubstituted organic πconjugated gem-diphenyldiethynylethylene (DPDEE), vinylphenyldiethynylethylene (VPDEE), and phenyltriethynylethylene (PTEE) derivatives by a stepwise process, which provides a flexible platform for the synthesis of complex π-bond enrichment frameworks that were difficult to synthesize by previous methods. The initial optical characterization revealed that the synthesized molecules exhibited aggregation-induced emission (AIE) properties, which further establishes the groundwork for future applications and enriches and advances the field of functional π-conjugated frameworks research.

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“…In addition, the Perkow reaction [68], which is based on the reaction of halogenated ketones with phosphites, can also be used to prepare vinyl phosphates (Scheme 2b). This is particularly advantageous for the preparation of triple [69,70] and double [71][72][73][74][75][76] electrophilic templates 6 using brominated ketone 5. Cross-coupling reactions are also useful for the introduction of simple fragmentsnamely, the vinyl group.…”

Section: Introductionmentioning

confidence: 99%

Vinyl Esters and Vinyl Sulfonates as Green Alternatives to Vinyl Bromide for the Synthesis of Monosubstituted Alkenes via Transition-Metal-Catalyzed Reactions

Tobrman

2023

Chemistry

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This review summarizes the applications of vinyl sulfonate and vinyl acetate as green alternatives for vinyl bromide in cross-coupling reactions. In the first part, the preparation of vinyl sulfonates and their cross-coupling reactions are briefly discussed. Then, a brief review of vinyl acetate cross-coupling reactions, including cyclization reactions, the Fujiware–Moritani reaction, and transvinylation reactions are described.

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The Synthesis of Tetrasubstituted Cycloalkenes Bearing π‐Conjugated Substituents and Their Optical Properties

Cited by 3 publications

References 53 publications

Organophosphates as Versatile Substrates in Organic Synthesis

Organophosphates as Versatile Substrates in Organic Synthesis

Unlocking Diverse π-Bond Enrichment Frameworks by the Synthesis and Conversion of Boronated Phenyldiethynylethylenes

Vinyl Esters and Vinyl Sulfonates as Green Alternatives to Vinyl Bromide for the Synthesis of Monosubstituted Alkenes via Transition-Metal-Catalyzed Reactions

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