[1,2]-Retro-Brook rearrangement induced by electrochemical reduction of silyl enolates DOI Open Access

Ban Kinoshita,

Saki Maejima,

Yuta Niki

et al.

Bulletin of the Chemical Society of Japan, Journal Year: 2024, Volume and Issue: 97(4)

Published: March 28, 2024

Abstract Electrochemical reduction of the trimethylsilyl enolates alkyl aryl ketones induces retro-Brook rearrangement to provide 1-aryl-1-trimethylsilylalkan-1-ols. The transformation proceeds through a sequence 1) single-electron silyl enolate, 2) protonation with phenol, 3) another form siloxy-substituted benzylic anion, and 4) pivotal rearrangement.

Language: Английский

[1,2]-Retro-Brook rearrangement induced by electrochemical reduction of silyl enolates DOI Open Access

Ban Kinoshita,

Saki Maejima,

Yuta Niki

et al.

Bulletin of the Chemical Society of Japan, Journal Year: 2024, Volume and Issue: 97(4)

Published: March 28, 2024

Abstract Electrochemical reduction of the trimethylsilyl enolates alkyl aryl ketones induces retro-Brook rearrangement to provide 1-aryl-1-trimethylsilylalkan-1-ols. The transformation proceeds through a sequence 1) single-electron silyl enolate, 2) protonation with phenol, 3) another form siloxy-substituted benzylic anion, and 4) pivotal rearrangement.

Language: Английский

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