Cross-Coupling Reactions of Double or Triple Electrophilic Templates for Alkene Synthesis

Edlová, Tereza; Čubiňák, Marek; Tobrman, Tomáš

doi:10.1055/s-0040-1707270

Cited by 12 publications

(1 citation statement)

References 54 publications

(53 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Beyond the realm of traditional methods, techniques involving transition-metal complexes [ 5 , 6 , 7 ], electrosynthesis [ 8 , 9 , 10 , 11 , 12 ], and photochemical transformations [ 13 , 14 , 15 ] are widely used. These developments have allowed for the preparation of a wide range of compounds as well as transformations that include the formation of C–C bonds [ 16 , 17 , 18 , 19 , 20 , 21 ], the synthesis of heterocyclic compounds [ 22 , 23 , 24 , 25 , 26 , 27 , 28 ], and the preparation of tetrasubstituted alkenes [ 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 ]. In addition to conventional starting compounds, organophosphates are increasingly utilized in organic synthesis, likely due to their availability.…”

Section: Introductionmentioning

confidence: 99%

Organophosphates as Versatile Substrates in Organic Synthesis

Oeser,

Tobrman

2024

Molecules

Self Cite

View full text Add to dashboard Cite

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.

show abstract

Section: Introductionmentioning

confidence: 99%

Organophosphates as Versatile Substrates in Organic Synthesis

Oeser,

Tobrman

2024

Molecules

Self Cite

View full text Add to dashboard Cite

show abstract

Cationic [1,5]‐Aryl Migrations of Propargyl Benzyl Ethers – A Stereospecific Approach to E‐ and Z‐Tetrasubstituted Olefins

Sadhukhan,

Nair,

Baire

2024

Adv Synth Catal

View full text Add to dashboard Cite

Abstract. Herein we report the discovery and development of the first example of a cationic [1,5]‐aryl migration reaction, through an unprecedented phenonium ions. This reaction does not require any acid, base, transition metal‐based catalyst or promoter, instead promoted by the water activated NXS reagents. It provides a highly diastereoselective and rapid access to the medicinally and biologically important tetra‐substituted olefins (allyl alcohols). The involvement of an ipso‐carbon, as well as the phenonium ion during this novel, cationic [1,5]‐aryl migration was strongly supported by the isolation of 2‐oxaspiro[5.5]undecane‐9‐ones. This methodology is highly tolerable for a wide range of propargyl‐benzyl ethers, resulting in a selective construction of structurally divergent library of mono‐halo‐tricarbon‐substituted alkenes. Synthetic application has also been demonstrated by converting two isomeric‐iodo‐olefins to respective E‐ and Z‐isomers of tamoxifen in a stereospecific manner.

show abstract

Synthesis of 2‐Substituted Cyclobutanones by a Suzuki Reaction and Dephosphorylation Sequence

Koudelka

Tobrman

2021

Eur J Org Chem

Self Cite

View full text Add to dashboard Cite

We report a novel process for the preparation of 2-substituted cyclobutanones. Such a method relies on the cross-coupling reaction of bromocyclobutenyl diethyl phosphate with either boronic acids or organozinc reagents. Dephosphorylation of the prepared 2-substituted cyclobutenyl phosphates affords 2substituted cyclobutanones. We observed that the course of the dephosphorylation reaction depends on the properties of the substituents found on the cyclobutene nucleus. The presence of groups capable of stabilizing the negative charge is necessary for ring opening of cyclobutanones. The scope of the reported process for the preparation of 2-substituted cyclobutanones has also been extended to the preparation of cyclobutenyl sulfides.

show abstract

Cross-Coupling Reactions of Double or Triple Electrophilic Templates for Alkene Synthesis

Cited by 12 publications

References 54 publications

Organophosphates as Versatile Substrates in Organic Synthesis

Organophosphates as Versatile Substrates in Organic Synthesis

Cationic [1,5]‐Aryl Migrations of Propargyl Benzyl Ethers – A Stereospecific Approach to E‐ and Z‐Tetrasubstituted Olefins

Synthesis of 2‐Substituted Cyclobutanones by a Suzuki Reaction and Dephosphorylation Sequence

Contact Info

Product

Resources

About