DDQ‐mediated Direct C(sp<sup>3</sup>)H Cyanation of Benzyl Ethers and 1,3‐Diarylpropenes under Solvent‐ and Metal‐free Conditions

Kong, Shanshan; Zhang, Lingqiong; Dai, Xiaoli; Tao, Lianzhi; Xie, Changde; Shi, Lei; Wang, Min

doi:10.1002/adsc.201500096

Cited by 24 publications

(3 citation statements)

References 67 publications

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“…Compounds 1 – 1 to 1 – 32 , 3 – 1 to 3 – 30 , and 3 – 33 to 3 – 34 were prepared according to the referenced literature …”

Section: Methodsmentioning

confidence: 99%

Single-Electron Reduction of “Push–Pull” C–C Single Bond and Decyanation Using Tertiary Amines as the Organic Electron Donor

Li,

Sun,

Zhang

et al. 2024

J. Org. Chem.

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Using commercially available tertiary amines as an organic electron donor (OED), the reduction of "push−pull" C−C single bond and reductive decyanation of tetrahydroisoquinolines were realized. These reactions exhibited higher reaction efficiency and better functional group tolerance compared with those of metallic reductants, and the mechanistic study indicated that a radical intermediate was involved in the reduction of the C−C single bond, which provides a new way to the OED-enabled mild reduction.

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“…Compounds 1 – 1 to 1 – 32 , 3 – 1 to 3 – 30 , and 3 – 33 to 3 – 34 were prepared according to the referenced literature …”

Section: Methodsmentioning

confidence: 99%

Single-Electron Reduction of “Push–Pull” C–C Single Bond and Decyanation Using Tertiary Amines as the Organic Electron Donor

Li,

Sun,

Zhang

et al. 2024

J. Org. Chem.

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“…Very recently, Huo and co-workers [73] reported the CBr4 mediated dehydrogenative coupling of isochromans with aromatic ketones, while Wo et al [74] demonstrated that the nucleophilic addition of β-keto esters to isochroman can be achieved by photoredoxneutral catalysis using a commercial dyad photosensitizer. Analogously thioethers [75] and ciano groups [76] can be introduced in the C(1) position via a CDC strategy using DTBP or DDQ as oxidant (Scheme 14, e). Amination and amidation [77] of isochroman can be obtained with FeCl3/TBHP or under metalfree conditions in the presence of DTBP (Scheme 14, f).…”

Section: Biological Properties Chemical Reactivity and Common Synthet...mentioning

confidence: 99%

Potentiality and Synthesis of O‐ and N‐Heterocycles: Pd‐Catalyzed Cyclocarbonylative Sonogashira Coupling as a Valuable Route to Phthalans, Isochromans, and Isoindolines

Albano

Aronica

2017

Eur J Org Chem

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Oxygen and Nitrogen-heterocyclic compounds are found in a vast number of natural substrates and biologically active molecules. In particular, phthalan, isochroman and isoindoline scaffolds are present in many classes of products such as antimicotics, antibiotics, antioxidants, pigments and fluorophores. Therefore several procedure dedicated to the buiding of such heterocycles have been developed. In this review a detailed analysis of literature data regarding these nuclei is described. Particular attention has been devoted to their biological and chemical potentialities and a deep investigation on the most important synthetic methods is reported. Cyclocarbonylative Sonogashira reaction of suitable alcohols and amides has been especially considered, since it represents a valuable and atom economic route to construct alkylidene phthalans, isochromans and isoindolines.Gianluigi Albano, born in Bari (Italy) in 1989, studied Chemistry at the University of Pisa (Italy), where he received his Master's Degree in February 2015. In November 2015 he started his PhD studies at the same university, under the supervision of Prof. Lorenzo Di Bari and Dr. Laura Antonella Aronica. His main research topics are focused on the synthesis and characterization of chiral conjugated oligomers for innovative optoelectronic applications and on the development of new protocols for the synthesis of heterocyclic compounds through transition metals-promoted reactions.Laura Antonella Aronica graduated cum laude in Chemistry in 1995 from the University of Pisa. In 1999 she obtained her Ph.D. in Chemical Sciences. During this period she spent six months as research assistant at University of Ottawa with Prof. Howard Alper. She is presently a researcher at the University of Pisa and her major research interests are concerned with organometallic chemistry directed towards organic synthesis and in particular with carbonylative cross coupling reactions and their application to the synthesis of heterocyclic compounds.

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“…The specific reactivity of 1,3-diphenylpropene is due to the presence of methylene group, being simultaneously in the allyl and benzyl positions. (E)-1,3-Diphenylpropene is usually obtained by treating a not easily accessible phenylacetaldehyde with a KOH alcohol solution [5,6], while the synthesis of less thermodynamically stable (Z)-isomer with an acceptable stereochemical purity is very problematic [7,8]. …”

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confidence: 99%

A Simple Synthesis of 1,3-Diphenylpropene

et al. 2018

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Abstract-A simple approach to the synthesis of 1,3-diphenylpropene isomers was developed based on Fe(acac) 3 -catalyzed cross-coupling of (E)-and (Z)-1,3-dichloropropenes with phenylmagnesium bromide.Keywords: 1,3-diphenylpropene, cross-coupling, Fe-catalyzed cross-coupling, Fe(acac) 3 ISSN 1070-3632, Russian Journal of General Chemistry, 2018, Vol. 88, No. 2, pp. 342-344. © Pleiades Publishing, Ltd., 2018. Original Russian Text © R.N. Shakhmaev, A.Sh. Sunagatullina, A.N. Vasilyeva, V.V. Zorin, 2018, published in Zhurnal Obshchei Khimii, 2018 1,3-Diphenylpropene isomers are used in organic synthesis as the starting substrates and model compounds [1][2][3][4]. The specific reactivity of 1,3-diphenylpropene is due to the presence of methylene group, being simultaneously in the allyl and benzyl positions. (E)-1,3-Diphenylpropene is usually obtained by treating a not easily accessible phenylacetaldehyde with a KOH alcohol solution [5,6], while the synthesis of less thermodynamically stable (Z)-isomer with an acceptable stereochemical purity is very problematic [7,8]. LETTERS TO THE EDITORWe investigated the possibility of obtaining 1,3-diphenylpropene 2 by Fe(acac) 3 -catalyzed crosscoupling of 1,3-dichloropropene 1 with phenylmagnesium bromide. It is known that available iron(III) salts are effective catalysts in cross-coupling reactions of Grignard reagents with vinyl [9--12] and allyl halides [13,14]. Fe(acac) 3 the most commonly used in the synthesis of natural compounds [15,16] and drugs [17][18][19][20] is advantageously characterized by low hygroscopicity, good solubility, and ease of handling [21].The reaction of (E)-1,3-dichloropropene la with 3 equiv of PhMgBr in tetrahydrofuran in the presence of 3 mol % of Fe(acac) 3 afforded a mixture of (E)-and (Z)-isomers of 1,3-diphenylpropene 2a and 2b (E : Z = 92 : 8) in a 52% yield. The introduction of the most frequently used ligands like N,N,N,N-tetramethylethylenediamine (TMEDA) [22] or N-methylpyrrolidone (NMP) [10], the replacement of THF by diethyl ether and the use of FeCl 3 as the catalyst did not substantially increase the yield of the reaction product. However, a decrease in the reaction temperature to -35°C results in an increase in the yield of 1,3-diphenylpropene to 80% with the same isomeric composition.The cross-coupling with (Z)-1,3-dichloropropene under similar conditions resulted in an isomeric mixture of 1,3-diphenylpropene (E : Z = 55 : 45) with 72% yield, while at room temperature the reaction direction shifted toward the formation of (E)-isomer (E : Z = 76 : 24). (E)-and (Z)-isomers of 1,3-diphenylpropene and diphenyl formed by homocoupling reaction were separated by column chromatography (Scheme 1).Structure and purity of the obtained compounds was confirmed by high-performance GLC analysis, NMR spectroscopy and chromato-mass spectrometry. A reliable evidence of the stereochemical configuration of isomers 2a and 2b was the values of spin-spin coupling constant of vinyl hydrogen atoms (J = 15.6 and 11.3 Hz), characteristic of the E-and Z-con...

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DDQ‐mediated Direct C(sp³)H Cyanation of Benzyl Ethers and 1,3‐Diarylpropenes under Solvent‐ and Metal‐free Conditions

Cited by 24 publications

References 67 publications

Single-Electron Reduction of “Push–Pull” C–C Single Bond and Decyanation Using Tertiary Amines as the Organic Electron Donor

Single-Electron Reduction of “Push–Pull” C–C Single Bond and Decyanation Using Tertiary Amines as the Organic Electron Donor

Potentiality and Synthesis of O‐ and N‐Heterocycles: Pd‐Catalyzed Cyclocarbonylative Sonogashira Coupling as a Valuable Route to Phthalans, Isochromans, and Isoindolines

A Simple Synthesis of 1,3-Diphenylpropene

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DDQ‐mediated Direct C(sp3)H Cyanation of Benzyl Ethers and 1,3‐Diarylpropenes under Solvent‐ and Metal‐free Conditions

Cited by 24 publications

References 67 publications

Single-Electron Reduction of “Push–Pull” C–C Single Bond and Decyanation Using Tertiary Amines as the Organic Electron Donor

Single-Electron Reduction of “Push–Pull” C–C Single Bond and Decyanation Using Tertiary Amines as the Organic Electron Donor

Potentiality and Synthesis of O‐ and N‐Heterocycles: Pd‐Catalyzed Cyclocarbonylative Sonogashira Coupling as a Valuable Route to Phthalans, Isochromans, and Isoindolines

A Simple Synthesis of 1,3-Diphenylpropene

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DDQ‐mediated Direct C(sp³)H Cyanation of Benzyl Ethers and 1,3‐Diarylpropenes under Solvent‐ and Metal‐free Conditions