Iron-catalyzed direct alkenylation of sp3(C–H) bonds via decarboxylation of cinnamic acids under ligand-free conditions

Yang, Hailong; Yan, Hong; Sun, Peng; Zhu, Yan; Lu, Linhua; Liu, Defu; Rong, Guangwei; Mao, Jincheng

doi:10.1039/c3gc37131j

Cited by 95 publications

(31 citation statements)

References 95 publications

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“…Addition of the radical scavenger 2,2,6,6-tetramethylpiperidine N -oxide (TEMPO) or azobisisobutyronitrile (AIBN) completely inhibited the reaction, and almost no desired product was obtained. Based on these results and literature reports [69–70], a plausible mechanism for the radical oxidative coupling is illustrated in Scheme 3. At the beginning, Fe-catalyzed cleavage of DTBP by Fe(III) in the presence of cinnamic acid, gives tert -butoxy radical A , intermediate B and one acac.…”

Section: Resultssupporting

confidence: 61%

Iron-catalyzed decarboxylative alkenylation of cycloalkanes with arylvinyl carboxylic acids via a radical process

Zhao¹,

Fang²,

Han³

et al. 2013

Beilstein J. Org. Chem.

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Section: Resultssupporting

confidence: 61%

Iron-catalyzed decarboxylative alkenylation of cycloalkanes with arylvinyl carboxylic acids via a radical process

Zhao¹,

Fang²,

Han³

et al. 2013

Beilstein J. Org. Chem.

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“…578 No ligands or other additives were required. Arylbenzylalkenes were obtained in moderate to good yields.…”

Section: Decarboxylative and Decarbonylativementioning

confidence: 99%

Iron Catalysis in Organic Synthesis

2015

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“…, acyl and ketonic radicals were reported. Toluene, boron reagents, aldehydes, acids, amides, ketones, ethers, alcohols, epoxides, nitriles were able to function as radical precursors.…”

Section: Radical Additionmentioning

confidence: 99%

“…In the presence of DTBP/TBHP, hydroxyl radical from TBHP afforded the β ‐hydroxy acid intermediates, which could be further converted to ketones. On the other hand, halogenoalkane, alkyl acids, N ‐(acyloxy) phthalimide, alkyl aldehydes, could aslo be utilized as alkyl radical precursors in the radical addition‐decarboxylation strategy (Scheme ).…”

Section: Radical Additionmentioning

confidence: 99%

Recent Advances of Cinnamic Acids in Organic Synthesis

et al. 2020

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The great success of cinnamic acids was rooted in their multiple functional groups. Herein, reactions triggered by the radical addition, electrophilic addition, Michael addition and reactions of acids were thoroughly discussed and summarized. Multi-component reactions, rearrange-ments, stereoselective synthesis, coupling, additions will be depicted in detail. This review focused on advances of cinnamic acids in the last decade (2010)(2011)(2012)(2013)(2014)(2015)(2016)(2017)(2018)(2019)(2020). We hope this review will be good for a better understanding of these reagents and future research. * , [7,8] acyl [9] and ketonic [10] radicals were reported. Toluene, [8a-c,9] boron reagents, [8d] aldehydes, [8e] acids, [9b,c] amides, [9d,12e-f] ketones, [10a-b] ethers, [11a-c] alcohols, [12a] epoxides, [12b] nitriles [12a] were able to function as radical precursors.Mao and co-workers [4] reported the decarboxylative methylation of cinnamic acids. The DTBP was employed not only as the oxidant, but also as the methyl source.C vinyl À CF 3 compounds (like Panomifene, and Cyhalothrin) were useful in medicinal chemistry. [5b] Hence, numerous efforts have been devoted to the preparation of these compounds. In this decade, several applications of air-stable Togni's reagent [5a-c,6a] or NaSO 2 CF 3 [5d-f,6b] for the direct C vinyl À CF 3 construction from cinnamic acids have been reported. These radical addition and decarboxylative methods usually required a metal-catalyst (Ir, [5a] Cu [5c,e,6b] ) (Scheme 3)Hu and co-workers [6a] presented a protocol for the construction of C sp2 À CF 2 SO 2 R bonds with a Togni-type reagent. The [a] L.Scheme 1. Classification by mechanism Scheme 2. Radical cascade.

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Iron-catalyzed direct alkenylation of sp3(C–H) bonds via decarboxylation of cinnamic acids under ligand-free conditions

Cited by 95 publications

References 95 publications

Iron-catalyzed decarboxylative alkenylation of cycloalkanes with arylvinyl carboxylic acids via a radical process

Iron-catalyzed decarboxylative alkenylation of cycloalkanes with arylvinyl carboxylic acids via a radical process

Iron Catalysis in Organic Synthesis

Recent Advances of Cinnamic Acids in Organic Synthesis

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