An autocatalytic cycle in autoxidation of triethylborane

Uematsu, Ryohei; Saka, Chihiro; Sumiya, Yosuke; Ichino, Tomoya; Taketsugu, Tetsuya; Maeda, Satoshi

doi:10.1039/c7cc02541f

Cited by 18 publications

(15 citation statements)

References 24 publications

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“…Trialkyl boranes readily undergo radical reactions generating alkyl radicals. Such processes can be initiated by oxygen, light or radical initiators, such as AIBN (Azobisisobutyronitrile) [54,55]. Additionally, ditellurides have been demonstrated to easily react with alkyl radicals, exhibiting remarkable radical-trapping activity [56].…”

Section: Resultsmentioning

confidence: 99%

Unexpected Ethyltellurenylation of Epoxides with Elemental Tellurium under Lithium Triethylborohydride Conditions

Tanini

Capperucci

2020

Chemistry

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The one-pot multistep ethyltellurenylation reaction of epoxides with elemental tellurium and lithium triethylborohydride is described. The reaction mechanism was experimentally investigated. Dilithium ditelluride and triethyl borane, formed from elemental tellurium and lithium triethylborohydride, were shown to be the key species involved in the reaction mechanism. Epoxides undergo ring-opening reaction with dilithium ditelluride to afford β-hydroxy ditellurides, which are sequentially converted into the corresponding β-hydroxy-alkyl ethyl tellurides by transmetalation with triethyl borane, reasonably proceeding through the SH2 mechanism.

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Section: Resultsmentioning

confidence: 99%

Unexpected Ethyltellurenylation of Epoxides with Elemental Tellurium under Lithium Triethylborohydride Conditions

Tanini

Capperucci

2020

Chemistry

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“…A recent work by density functional theory calculations proposed that the autoxidation was an autocatalytic process in which the alkyl radical acted as a catalyst. 20 The initiation step between trialkylborane and oxygen had limited role for formation of alkyl radical. It is noteworthy that the alkyl radical was dominant and acted as activating species in radical reaction.…”

Section: As Radical Initiators In Conventional and Pseudoliving Radicmentioning

confidence: 99%

“…Besides the reactions mentioned above, other processes and intermediates might also be involved. A recent work by density functional theory calculations proposed that the autoxidation was an autocatalytic process in which the alkyl radical acted as a catalyst . The initiation step between trialkylborane and oxygen had limited role for formation of alkyl radical.…”

Section: Introductionmentioning

confidence: 99%

Alkylboranes in Conventional and Controlled Radical Polymerization

Pan

2019

Journal of Polymer Science

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Utilizations of alkylboranes reagents in radical polymerization are summarized in this minireview. Alkylboranes act as conventional radical initiators or radical chain‐transfer agents in free‐radical polymerization and controlled radical polymerization. This review discusses various polymerizations operating through different alkylborane reagents with their accompanying mechanisms. The aim of this minireview is to present the state of art of alkylboranes in radical polymerization and to provide the future aspects of this direction. © 2019 Wiley Periodicals, Inc. J. Polym. Sci. 2020, 58, 14–19

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“…[7] Ar ecent theoretical study hass upported that it is autocatalyticint he alkyl radical. [59] The high reactivity of borane autoxidation makest his system the methodo fc hoice for radical reactions at very low temperatures. For example, the polymerization of vinyl chloride has been shown to be feasible even at À78 8C.…”

Section: Trialkylborane Initiatorsmentioning

confidence: 99%

Molecular Radical Chain Initiators for Ambient‐ to Low‐Temperature Applications

Székely

Klußmann

2018

Chemistry An Asian Journal

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An overview of methodsf or the initiation of radical chain reactions by specific initiator compounds, which generate radicals, is given. These can be utilized to initiate any kind of radical chain reactionb yt ransforming substrates into the desired radical intermediates. Azo initiators,p eroxides, nitroxides, trialkylboranes, dialkyl zinc compounds, and type Ip hotoinitiators are discussed, as well as methods of redox-and sonochemical initiation. Methods of direct radical formation from the substrates, such as photoredoxc atalysis or high-energyi rradiation, are not included. The focus of this review lies on rather "low" temperatures in the range of 50 8Cd own to À78 8C, which can be useful to achievem ore selectiver eactions. Illustrative applications of such radical chain initiatorsi navariety of reactions are discussed, including stereoselective ones and polymerizations.Scheme1.Generalmechanism for radical chain reactions transforming substrates (S) into product (P) via intermediate radicals (iR), being initiatedw ith radicals generated from molecularinitiatorsX -Y.Scheme2.Classification of radicalgeneration from initiator molecules X-Y (D:thermal energy;h n:photochemically;)))): sonochemically).Scheme19. Applications of type-I photoinitiators in organics ynthesis.Scheme20. Initiation of athiol-enereaction with N-phenyltriazolinedione 40.Scheme21. Sonochemical initiation of radical reactions.

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An autocatalytic cycle in autoxidation of triethylborane

Cited by 18 publications

References 24 publications

Unexpected Ethyltellurenylation of Epoxides with Elemental Tellurium under Lithium Triethylborohydride Conditions

Unexpected Ethyltellurenylation of Epoxides with Elemental Tellurium under Lithium Triethylborohydride Conditions

Alkylboranes in Conventional and Controlled Radical Polymerization

Molecular Radical Chain Initiators for Ambient‐ to Low‐Temperature Applications

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