Electrochemical Arene Radical Cation Promoted Spirocyclization of Biaryl Ynones: Access to Alkoxylated Spiro[5,5]trienones

Zhou, Wei; Li, Zi-Qiong; Cheng, Chaozhihui; Lu, Lin; Yang, Ruchun; Song, Xian-Rong; Luo, Mu-Jia; Xiao, Qiang

doi:10.1021/acs.orglett.3c03678

Org. Lett.

2023

DOI: 10.1021/acs.orglett.3c03678

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Electrochemical Arene Radical Cation Promoted Spirocyclization of Biaryl Ynones: Access to Alkoxylated Spiro[5,5]trienones

Wei Zhou,

Zi-Qiong Li,

Chaozhihui Cheng

et al.

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2024

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Synthesis of Sulfonyl‐Containing spiro[5,5]trienones from Sodium Metabisulfite

Xiao,

Tang,

et al. 2024

Adv Synth Catal

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An efficient three‐component reaction of biaryl ynones, sodium metabisulfite and aryldiazonium tetrafluoroborates is developed. The reaction occurs at room temperature without any additives, thus offering a sustainable approach to access sulfonyl‐containing spiro[5,5]trienones. This protocol features mild conditions, broad substrate scope and high functional group compatibility, furnishing the target products in moderate to good yields. Mechanistic studies indicate that the reaction undergoes a 6‐exo‐trig dearomative spirocyclization process which is initated by an aryl radical with the insertion of sulfur dioxide.

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Synthesis of Sulfonyl‐Containing spiro[5,5]trienones from Sodium Metabisulfite

Xiao,

Tang,

et al. 2024

Adv Synth Catal

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Electrochemical Arene Radical Cation Promoted Spirocyclization of Biaryl Ynones: Access to Alkoxylated Spiro[5,5]trienones

Cited by 1 publication

References 59 publications

Synthesis of Sulfonyl‐Containing spiro[5,5]trienones from Sodium Metabisulfite

Synthesis of Sulfonyl‐Containing spiro[5,5]trienones from Sodium Metabisulfite

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