Novel synthesis of alkenes via triethylaluminum-induced free radical reactions of alkyl iodides and β-nitrostyrenes

Liu, Jing-Yuan; Liu, Ju‐Tsung; Yao, Ching‐Fa

doi:10.1016/s0040-4039(01)00519-6

Cited by 24 publications

(12 citation statements)

References 39 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…266 The nitrostyrene radical-addition/elimination paradigm is known in the literature to proceed under a variety of radical-generation methods including diazo thermolysis, 318 the action of alkyl-gallium, 319 -borane 320 and -aluminum 321 species, and peroxide homolysis. 322 It also should be noted that similar radical-addition-elimination sequences have been shown to take place utilizing a number of other β -styrene substituents as single electron nucleofuges.…”

Section: C-c Bondsmentioning

confidence: 99%

Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins

et al. 2016

View full text Add to dashboard Cite

Cofactor-mimetic aerobic oxidation has conceptually merged with catalysis of syngas reactions to form a wide range of Markovnikov-selective olefin radical hydrofunctionalizations. We cover the development of the field and review contributions to reaction invention, mechanism and application to complex molecule synthesis. We also provide a mechanistic framework for understanding this compendium of radical reactions.

show abstract

Section: C-c Bondsmentioning

confidence: 99%

Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins

et al. 2016

View full text Add to dashboard Cite

show abstract

“…We commenced our investigation by reacting (À)-isopulegol (1a)a samodel alkene with ar ange of structurally diverse vinylation agents:( E)-(2-bromovinyl)benzene (2), [18] cinnamic acid (3), [19] two b-nitrostyrenes 4, [20] (E)-[2-(benzenesulfonyl)vinyl]benzene (5), [21] (E)-1-styryl-1,2-benziodoxol-3(1H)-one (6) [22] (entries 1-6, Table 1). Among them, 4methyl-b-nitrostyrene (4b)performed the best, providing the desired styrylated cyclohexanol 7ab in 47 %y ield (entry 4).…”

Section: Resultsmentioning

confidence: 99%

Dealkenylative Alkenylation: Formal σ‐Bond Metathesis of Olefins

et al. 2020

View full text Add to dashboard Cite

The dealkenylative alkenylation of alkene C(sp3)−C(sp2) bonds has been an unexplored area for C−C bond formation. Herein 64 examples of β‐alkylated styrene derivatives, synthesized through the reactions of readily accessible feedstock olefins with β‐nitrostyrenes by ozone/FeII‐mediated radical substitutions, are reported. These reactions proceed with good efficiencies and high stereoselectivities under mild reaction conditions and tolerate an array of functional groups. Also demonstrated is the applicability of the strategy through several synthetic transformations of the products, as well as the syntheses of the natural product iso‐moracin and the drug (E)‐metanicotine.

show abstract

“…Although each proposal differs in detail, the main three characteristic steps feature in all proposals. Firstly, carbon- or heteroatom-centered radical 4 is generated in situ by various methods from precursors 6 – 33 [ 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 ]. These include a thermal homolytic cleavage of labile bonds, metal-catalyzed and photochemically initiated processes.…”

Section: Nitrostyrene Cross-coupling—the Background and Mechanismsmentioning

confidence: 99%

Denitrative Cross-Couplings of Nitrostyrenes

et al. 2020

View full text Add to dashboard Cite

Interestingly, β-nitrostyrenes, typically bench stable compounds, are highly promising cross-coupling partners, due to their excellent availability and well understood reactivity. In this review, we report on the discovery and advancements, in the field of stereoselective, denitrative cross-couplings of β-nitrostyrenes with miscellaneous organic reagents. The rapidly expanding field offers alternative access to a broad range of functionalized alkenes, including β-alkylated styrenes, chalcones, stilbenes, cinnamic acids, and conjugated sulfones and phosphonates. The most important mechanistic pathways are briefly discussed, to familiarize readers with the elementary reactions occurring during the coupling.

show abstract

Novel synthesis of alkenes via triethylaluminum-induced free radical reactions of alkyl iodides and β-nitrostyrenes

Cited by 24 publications

References 39 publications

Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins

Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins

Dealkenylative Alkenylation: Formal σ‐Bond Metathesis of Olefins

Denitrative Cross-Couplings of Nitrostyrenes

Contact Info

Product

Resources

About