(E)-Specific direct Julia-olefination of aryl alcohols without extra reducing agents promoted by bases

Yao, Chuan‐Zhi; Li, Qiang‐Qiang; Wang, Meimei; Ning, Xiaojuan; Kang, Yan‐Biao

doi:10.1039/c5cc01965f

Cited by 42 publications

(28 citation statements)

References 52 publications

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“…Spectral data were consistent with literature-reported values. 33 1 H NMR (400 MHz, CDCl 3 ) δ 7.56 (s, 1H), 7.41–7.35 (m, 1H), 7.35–7.29 (m, 1H), 7.19 (t, J = 7.8 Hz, 1H), 6.65 (dd, J = 17.6, 10.9 Hz, 1H), 5.76 (d, J = 17.6 Hz, 1H), 5.30 (d, J = 10.9 Hz, 1H). 13 C NMR (100 MHz, CDCl 3 ) δ 139.8, 135.6, 130.8, 130.2, 129.3, 125.0, 122.9, 115.5.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of 1,3-Substituted Cyclobutanes by Allenoate-Alkene [2 + 2] Cycloaddition

Conner

Brown

2016

J. Org. Chem.

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Section: Methodsmentioning

confidence: 99%

Synthesis of 1,3-Substituted Cyclobutanes by Allenoate-Alkene [2 + 2] Cycloaddition

Conner

Brown

2016

J. Org. Chem.

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“…Recently, the olefination of alcohols with sulfones via a Julia‐type reaction catalyzed by pincer PNN ruthenium complexes has been described . Right after, a similar process was reported to occur in the only presence of a base . Initially, the reaction of phenyl methyl sulfone with benzyl alcohol, used in excess and as a solvent, was performed with a variety of bases (KO t ‐Bu, NaO t ‐Bu, NaH, NaHMe, KOH, n ‐BuLi, and LiHMDS) at 130‐135 °C under an argon atmosphere.…”

Section: Tm‐free Dehydrative C−c Forming Reactions With Alcoholsmentioning

confidence: 99%

Base‐Mediated Transition‐Metal‐Free Dehydrative C−C and C−N Bond‐Forming Reactions from Alcohols

Porcheddu

Chelucci

2019

The Chemical Record

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In recent years, there has been an increasing interest in using alcohols as alkylating agents for C−C and C−N bond‐forming processes employing mainly TM‐catalysts. Although BH‐catalysis looks like a green atom economy process since water is the only by‐product, it often suffers from one or more drawbacks, such as the use of expensive noble metal complexes, capricious ligands, and toxic organic solvents. Therefore, straightforward, efficient, atom economy and environmentally benign alternative protocols are desirable. This review aims to summarize the current knowledge within the published literature about dehydrative processes developed without TM‐catalysts. The most recent contributions to this topic have been reviewed keeping into account the new findings reported in this area. The features, strengths, and limitations of these alcohol‐based C−C and C−N bond‐forming processes has also been taken into account.

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“…[11] Although the Julia olefination of alcohols is potentially attractive, the reported methods are only applicable to activated (benzyl, naphthyl) primary alcohols and are not effectivef or the olefination of primarya liphatic and secondary alcohols. [9,11] The only example of ac atalytic Julia olefination of primary alcohols [9] suffers from al ow turnover number (TON) and difficulties in catalyst/product separationa nd reuse of the homogeneous Ru catalyst. As ap art of our continuing interest in the heterogeneousc atalysis for bond formation reactions that are driven by the acceptorless dehydrogenationo fa lcohols, [12] we report herein ah eterogeneous catalytic system for the direct olefinationo fv arious primary and secondary alcohols with sulfones by using catalytic Pt nanoparticles loaded on carbon (Pt/C).…”

Section: Introductionmentioning

confidence: 99%

Direct Olefination of Alcohols with Sulfones by Using Heterogeneous Platinum Catalysts

Siddiki

Touchy

Kon

et al. 2016

Chemistry A European J

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Carbon-supported Pt nanoparticles (Pt/C) were found to be effective heterogeneous catalysts for the direct Julia olefination of alcohols in the presence of sulfones and KOtBu under oxidant-free conditions. Primary alcohols, including aryl, aliphatic, allyl, and heterocyclic alcohols, underwent olefination with dimethyl sulfone and aryl alkyl sulfones to give terminal and internal olefins, respectively. Secondary alcohols underwent methylenation with dimethyl sulfone. Under 2.5 bar H2, the same reaction system was effective for the transformation of alcohol OH groups to alkyl groups. Structural and mechanistic studies of the terminal olefination system suggested that Pt(0) sites on the Pt metal particles are responsible for the rate-limiting dehydrogenation of alcohols and that KOtBu may deprotonate the sulfone reagent. The Pt/C catalyst was reusable after the olefination, and this method showed a higher turnover number (TON) and a wider substrate scope than previously reported methods, which demonstrates the high catalytic efficiency of the present method.

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(E)-Specific direct Julia-olefination of aryl alcohols without extra reducing agents promoted by bases

Cited by 42 publications

References 52 publications

Synthesis of 1,3-Substituted Cyclobutanes by Allenoate-Alkene [2 + 2] Cycloaddition

Synthesis of 1,3-Substituted Cyclobutanes by Allenoate-Alkene [2 + 2] Cycloaddition

Base‐Mediated Transition‐Metal‐Free Dehydrative C−C and C−N Bond‐Forming Reactions from Alcohols

Direct Olefination of Alcohols with Sulfones by Using Heterogeneous Platinum Catalysts

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