Copper catalyzed direct alkenylation of simple alkanes with styrenes

Zhu, Yefeng; Wei, Yunyang

doi:10.1039/c4sc00093e

Cited by 119 publications

(43 citation statements)

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“…In addition, MS analysis indicated the presence of 2,2,6,6-tetramethyl-1-(tetrahydrofuran-2-yloxy) piperidine as an intermediate in the reaction mixture (Scheme 2a). On the basis of all these results and previous reports, [8,[43][44][45][46][47] a reaction pathway is proposed as described in Scheme 2b. Initially, tert-butoxy radical would be formed through the cleavage of DTBP with the assistance of the perovskite catalyst.…”

Section: S C H E M Esupporting

confidence: 61%

Direct oxidative C(sp³)─H/C(sp²)─H coupling reaction using recyclable Sr‐doped LaCoO₃ perovskite catalyst

Trinh

Tran

Nguyễn

et al. 2020

Applied Organom Chemis

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A strontium‐doped lanthanum cobaltite perovskite, La0.6Sr0.4CoO3, was prepared and utilized as a recyclable heterogeneous catalyst for the direct oxidative C(sp3)─H/C(sp2)─H coupling reaction between cyclic ethers and alkenes or coumarins to achieve corresponding α‐functionalized ethers. The α‐functionalization of cyclic thioethers or amides with alkenes or coumarins was also achieved via this protocol. The La0.6Sr0.4CoO3 catalyst exhibited better performance than a variety of homogeneous and heterogeneous catalysts. Utilizing a recyclable catalyst would offer a greener option for the direct oxidative C(sp3)─H/C(sp2)─H coupling reaction. To our best knowledge, the C(sp3)─H/C(sp2)─H coupling between olefins and ethers to generate α‐functionalized ethers using a heterogeneous catalyst has not been previously reported, and the α‐functionalization of cyclic thioethers or amides with alkenes or coumarins is new.

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Section: S C H E M Esupporting

confidence: 61%

Direct oxidative C(sp³)─H/C(sp²)─H coupling reaction using recyclable Sr‐doped LaCoO₃ perovskite catalyst

Trinh

Tran

Nguyễn

et al. 2020

Applied Organom Chemis

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“…29 Similar to the work by Lei, DTBP was utilized as the oxidant. The copper catalyst Cu(OTf) 2 was crucial in this transformation.…”

Section: View Article Onlinementioning

confidence: 99%

Olefinic C–H functionalization through radical alkenylation

et al. 2015

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Direct olefinic C-H functionalization represents the ideal way of introducing an alkenyl group into organic molecules. A well-known process is the Heck reaction, which involves alkene insertion and β-hydride elimination in the presence of a transition metal. However, the traditional Heck reaction mainly deals with the alkenylation of aryl or vinyl electrophiles. Recent developments have revealed that alkenylation can also be achieved through radical addition to alkenes and following single-electron-transfer (SET) oxidation/elimination. The radical alkenylation pathway allows alkenylation with a variety of carbon-centered radicals and even heteroatom-centered radicals. This tutorial review gives an overview of recent advances in this emerging field.

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“…7 Wei reported a novel copper-catalyzed direct alkenylation of simple alkanes with styrenes to give (E)-alkyl substituted alkenes (Scheme 2, (a)). 8 Han revealed a metal-free oxidative C(sp 3 )−H bond activation of alkanes and conjugate addition to chromones (Scheme 2, (b)). 9 Han has also developed a novel synthesis of cycloallyl esters from cycloalkanes and aromatic aldehydes via copper-catalyzed C(sp 3 )−H bond activation (Scheme 2, (c)).…”

Section: Introductionmentioning

confidence: 98%

Synthesis of Ketones through Microwave Irradiation Promoted Metal-Free Alkylation of Aldehydes by Activation of C(sp³)–H Bond

et al. 2015

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In this paper, a novel methodology for the synthesis of ketones via microwave irradiation promoted direct alkylation of aldehydes by activation of the inert C(sp(3))-H bond has been developed. Notably, the reactions were accomplished under metal-free conditions and used commercially available aldehydes and cycloalkanes as substrates without prefunctionalization. By using this novel method, an alternative synthetic approach toward the key intermediates for the preparation of the pharmaceutically valuable oxaspiroketone derivatives was successfully established.

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Copper catalyzed direct alkenylation of simple alkanes with styrenes

Abstract: Copper Catalyzed Direct Alkenylation of Simple Alkanes with Styrenes. -The reaction is conducted under mild, user-friendly, and operationally simple conditions. -(ZHU, Y.; WEI*, Y.; Chem. Sci. 5 (2014) 6, 2379-2382,

Cited by 119 publications

References 35 publications

Direct oxidative C(sp³)─H/C(sp²)─H coupling reaction using recyclable Sr‐doped LaCoO₃ perovskite catalyst

Direct oxidative C(sp³)─H/C(sp²)─H coupling reaction using recyclable Sr‐doped LaCoO₃ perovskite catalyst

Olefinic C–H functionalization through radical alkenylation

Synthesis of Ketones through Microwave Irradiation Promoted Metal-Free Alkylation of Aldehydes by Activation of C(sp³)–H Bond

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Copper catalyzed direct alkenylation of simple alkanes with styrenes

Abstract: Copper Catalyzed Direct Alkenylation of Simple Alkanes with Styrenes. -The reaction is conducted under mild, user-friendly, and operationally simple conditions. -(ZHU, Y.; WEI*, Y.; Chem. Sci. 5 (2014) 6, 2379-2382,

Cited by 119 publications

References 35 publications

Direct oxidative C(sp3)─H/C(sp2)─H coupling reaction using recyclable Sr‐doped LaCoO3 perovskite catalyst

Direct oxidative C(sp3)─H/C(sp2)─H coupling reaction using recyclable Sr‐doped LaCoO3 perovskite catalyst

Olefinic C–H functionalization through radical alkenylation

Synthesis of Ketones through Microwave Irradiation Promoted Metal-Free Alkylation of Aldehydes by Activation of C(sp3)–H Bond

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Direct oxidative C(sp³)─H/C(sp²)─H coupling reaction using recyclable Sr‐doped LaCoO₃ perovskite catalyst

Direct oxidative C(sp³)─H/C(sp²)─H coupling reaction using recyclable Sr‐doped LaCoO₃ perovskite catalyst

Synthesis of Ketones through Microwave Irradiation Promoted Metal-Free Alkylation of Aldehydes by Activation of C(sp³)–H Bond