Transition metal catalyzed [6 + 2] cycloadditions

Ȧnand, Amit; Singh, Prabhpreet; Kumar, V. Pavan; Bhargava, Gaurav

doi:10.1039/c9ra02839k

Cited by 13 publications

(4 citation statements)

References 131 publications

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“…For example, transition metalbased catalysts have been discovered for the thermochemical [4 + 2] and [2 + 2] cycloaddition reactions. [22][23][24][25][26][27] To avoid higher price and toxicity, metal-free catalysts also have been invented in thermochemical reactions. [28][29][30] Parallel to the thermochemical reactions, photocatalytic cycloaddition reactions are also becoming popular due to their high synthetic utility.…”

Section: Introductionmentioning

confidence: 99%

Deal;Photoredox Catalysis for the Cycloaddition Reactions

Zhang

Das

2020

ChemCatChem

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Cycloaddition reaction is a powerful tool for the synthesis of cyclic structures in a green way. High‐energy ultraviolet (UV) light was strictly required for the traditional photochemical processes. However, in the past ten years, discovery of photoredox catalysis for the cycloaddition reactions have attracted significant attention. Based on these elegant works, this review will summarize recent progresses in the visible‐light‐induced [2+2] and [4+2] cycloaddition reactions.

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Section: Introductionmentioning

confidence: 99%

Deal;Photoredox Catalysis for the Cycloaddition Reactions

Zhang

Das

2020

ChemCatChem

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“…As shown by analysis of the published data, metal-promoted and metal-catalyzed cycloaddition reactions of 1,3,5-cycloheptatriene (CHT) to various unsaturated compounds are currently used as an alternative and successive approach to the synthesis of bicyclo[4.2.1]nonanes. 2j , 3 These reactions are described in the studies devoted to photo- and thermal- induced cyclocodimerization of Fe-, Ru-, Cr-, and Mo-containing CHT carbonyl complexes with alkenes, dienes, and alkynes. 4 − 7 The catalytic versions of these transformations include Ti-, Co-, Mo-, Rh-, and Pt-catalyzed cycloaddition reactions of CHT and its derivatives.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Functionally Substituted Bicyclo[4.2.1]nona-2,4-dienes and Bicyclo[4.2.1]nona-2,4,7-trienes by Cobalt(I)-catalyzed [6π + 2π] Cycloaddition of 2-Tropylcyclohexanone

et al. 2020

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The [6π + 2π] cycloaddition of 2-tropylcyclohexanone to allenes and alkynes was accomplished for the first time using the three-component catalytic system Co(acac)2(dppe)/Zn/ZnI2, thus giving previously unknown functionally substituted bicyclo[4.2.1]nona-2,4-dienes and bicyclo[4.2.1]nona-2,4,7-trienes in high yields (70–89%). The structures of the synthesized carbocycles were reliably proved using modern spectral methods and X-ray diffraction. The in vitro cytotoxic activity of the obtained bicyclo[4.2.1]nona-2,4-dienes and bicyclo[4.2.1]nona-2,4,7-trienes against the Jurkat, K562, and U937 tumor cell lines has been studied.

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“…1d) 36 , reactions of CHTs with nitroso compounds were revealed to cause a remarkable suprafacial [ π 6 s + π 2 s ]-cycloaddition that is thermally forbidden based on Woodward-Hoffmann rules [37][38][39] . Previous studies used nitroso compounds as dienophiles in [4 + 2]-cycloadditions [40][41][42][43][44] , even in reactions with CHTs 45 . The [6 + 2]-cycloaddition involving nitroso compounds remains elusive (up to 35% yield 46,47 , up to 49% ee 48 ), and no detailed mechanistic studies have been reported.…”

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confidence: 99%

Valence-isomer selective cycloaddition reaction of cycloheptatrienes-norcaradienes

Harada,

Takenaka,

Ito

et al. 2024

Nat Commun

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The rapid and precise creation of complex molecules while controlling multiple selectivities is the principal objective in synthetic chemistry. Combining data science and organic synthesis to achieve this goal is an emerging trend, but few examples of successful reaction designs are reported. We develop an artificial neural network regression model using bond orbital data to predict chemical reactivities. Actual experimental verification confirms cycloheptatriene-selective [6 + 2]-cycloaddition utilizing nitroso compounds and norcaradiene-selective [4 + 2]-cycloaddition reactions employing benzynes. Additionally, a one-pot asymmetric synthesis is achieved by telescoping the enantioselective dearomatization of non-activated benzenes and cycloadditions. Computational studies provide a rational explanation for the seemingly anomalous occurrence of thermally prohibited suprafacial [6 + 2]-cycloaddition without photoirradiation.

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Transition metal catalyzed [6 + 2] cycloadditions

Abstract: The [6 + 2] cycloaddition reactions are one of the important synthetic transformations to construct eight membered carbo-/heterocyclic systems.

Cited by 13 publications

References 131 publications

Deal;Photoredox Catalysis for the Cycloaddition Reactions

Deal;Photoredox Catalysis for the Cycloaddition Reactions

Synthesis of Functionally Substituted Bicyclo[4.2.1]nona-2,4-dienes and Bicyclo[4.2.1]nona-2,4,7-trienes by Cobalt(I)-catalyzed [6π + 2π] Cycloaddition of 2-Tropylcyclohexanone

Valence-isomer selective cycloaddition reaction of cycloheptatrienes-norcaradienes

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