Indium-promoted butenolide synthesis through consecutive C–C and C–O bond formations in aqueous tetrahydrofuran enabled by radicals

Almendros, Pedro; Yanai, Hikaru; Márquez, M. Rosa; Cembellín, Sara; Campo, Teresa Martínez del

doi:10.1039/d3qo00133d

Org. Chem. Front.

2023

DOI: 10.1039/d3qo00133d

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Indium-promoted butenolide synthesis through consecutive C–C and C–O bond formations in aqueous tetrahydrofuran enabled by radicals

Pedro Almendros

Hikaru Yanai

M. Rosa Márquez

et al.

Abstract: An indium-promoted lactonization of (indol-3-yl)-2-oxoacetaldehydes, which allows the synthesis of substituted γ-methylenebutenolides in aqueous environment, has been accomplished. This process is in clear contrast with the established metal-mediated reactivity of...

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Cited by 4 publications

(1 citation statement)

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“…In this context, we envisioned the regioselective preparation of relevant 1,3-dienes exploiting our previous experience on manganese C–H activation and allene reactivity . Allenes, with two orthogonal CC double bonds, play an important role in transition-metal-catalyzed transformations thanks to the strong affinity of C–metal nucleophiles for π-bonds.…”

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confidence: 99%

Regioselectivity Control in the Synthesis of Linear Conjugated Dienes Enabled by Manganese(I)-Catalyzed C–H Activation

Matesanz,

Gamarra,

del Campo

et al. 2023

ACS Catal.

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A highly selective Mn(I)-catalyzed dienylation of arenes and heteroarenes with acetylated allenes is described. The reported transformation proceeds by a simple one-pot procedure and delivers linear 1,3-dienes as single products with high stereoselectivity and total regioselectivity. A great variety of allenic substrates bearing diverse substitution patterns can be applied in this protocol where the insertion step occurs at the terminal carbon of the allene coupling partner, in contrast with the former preparations of dienes through C–H activation. This practical strategy features wide functional group tolerance and preparative scale utility showing very good efficiency in the late-stage functionalization of complex valuable molecules. Furthermore, the synthetic importance of the method is highlighted by different derivatizations of the final products, which can exhibit interesting fluorescence properties.

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confidence: 99%

Regioselectivity Control in the Synthesis of Linear Conjugated Dienes Enabled by Manganese(I)-Catalyzed C–H Activation

Matesanz,

Gamarra,

del Campo

et al. 2023

ACS Catal.

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Electrosynthesis of dimeric butenolides by C-C-homocoupling in the oxidation of 2,4-diarylfurans under aqueous conditions

Batanero,

Salardon,

Prieto-Garcés

et al. 2024

iScience

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Indium-Mediated Preparation of Bis(α-hydroxyallenes) or α,α′-Dihydroxyallenynes and Further Gold-Catalyzed Cyclizations

Martínez del Campo,

San Martín,

Gamarra

et al. 2024

J. Org. Chem.

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Indium-promoted butenolide synthesis through consecutive C–C and C–O bond formations in aqueous tetrahydrofuran enabled by radicals

Abstract: An indium-promoted lactonization of (indol-3-yl)-2-oxoacetaldehydes, which allows the synthesis of substituted γ-methylenebutenolides in aqueous environment, has been accomplished. This process is in clear contrast with the established metal-mediated reactivity of...

Cited by 4 publications

References 65 publications

Regioselectivity Control in the Synthesis of Linear Conjugated Dienes Enabled by Manganese(I)-Catalyzed C–H Activation

Regioselectivity Control in the Synthesis of Linear Conjugated Dienes Enabled by Manganese(I)-Catalyzed C–H Activation

Electrosynthesis of dimeric butenolides by C-C-homocoupling in the oxidation of 2,4-diarylfurans under aqueous conditions

Indium-Mediated Preparation of Bis(α-hydroxyallenes) or α,α′-Dihydroxyallenynes and Further Gold-Catalyzed Cyclizations

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