Sulfur Ylides as
            <scp>C</scp>
            1 Homologating Reagents

Spiliopoulou, Nikoleta; Nikitas, Nikolaos F.; Kokotos, Christoforos G.

doi:10.1002/9783527830237.ch8

Homologation Reactions 2023

DOI: 10.1002/9783527830237.ch8

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Sulfur Ylides as C 1 Homologating Reagents

Nikoleta Spiliopoulou

Nikolaos F. Nikitas

Christoforos G. Kokotos

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2024

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Cited by 2 publications

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Unveiling a Strategy for Ring Opening of Epoxides: Synthesis of 2-Hydroxyindolinylidenes Using α-Ester Sulfoxonium Ylides

Camara,

da Silva,

da Luz

et al. 2024

Org. Lett.

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The untapped potential of α-carbonyl sulfoxonium ylides in epoxide ring-opening reactions has been a notable gap in current research, with such reactivity predominantly associated with the highly reactive dimethylsulfoxonium methylide. This study introduces an innovative approach wherein an epoxide indole, formed in situ from 2-hydroxyindoline-3-triethylammonium bromide, undergoes reaction with α-ester sulfoxonium ylides. The outcome is the efficient synthesis of a range of 2-hydroxyindolin-3-ylidenes, demonstrating favorable yields (41−81%) and Z/E ratios from 4:1 to those of exclusive Z isomers. Additionally, the photophysical properties of the synthesized indolinylidenes are explored, along with their derivatization using various nucleophiles under acid catalysis.

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Unveiling a Strategy for Ring Opening of Epoxides: Synthesis of 2-Hydroxyindolinylidenes Using α-Ester Sulfoxonium Ylides

Camara,

da Silva,

da Luz

et al. 2024

Org. Lett.

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Synthesis of indolines via palladium-catalyzed [4 + 1] annulation of (2-aminophenyl)methanols with sulfoxonium ylides

Hao,

Kong,

et al. 2024

Org. Biomol. Chem.

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Sulfur Ylides as C 1 Homologating Reagents

Cited by 2 publications

References 101 publications

Unveiling a Strategy for Ring Opening of Epoxides: Synthesis of 2-Hydroxyindolinylidenes Using α-Ester Sulfoxonium Ylides

Unveiling a Strategy for Ring Opening of Epoxides: Synthesis of 2-Hydroxyindolinylidenes Using α-Ester Sulfoxonium Ylides

Synthesis of indolines via palladium-catalyzed [4 + 1] annulation of (2-aminophenyl)methanols with sulfoxonium ylides

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