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Oxalates as Activating Groups for Alcohols in Visible Light Photoredox Catalysis: Formation of Quaternary Centers by Redox-Neutral Fragment Coupling.

ABSTRACT: Alkyl oxalates are new bench-stable alcohol-activating groups for radical generation under visible light photoredox conditions. Using these precursors, the first net redox-neutral coupling of tertiary and secondary alcohols with electron-deficient alkenes is achieved.

SUBMITTER: Nawrat CC

PROVIDER: S-EPMC4632490 | biostudies-literature | 2015 Sep

REPOSITORIES: biostudies-literature

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Oxalates as Activating Groups for Alcohols in Visible Light Photoredox Catalysis: Formation of Quaternary Centers by Redox-Neutral Fragment Coupling.

Nawrat Christopher C CC Jamison Christopher R CR Slutskyy Yuriy Y MacMillan David W C DWC Overman Larry E LE

Journal of the American Chemical Society 20150831 35

Alkyl oxalates are new bench-stable alcohol-activating groups for radical generation under visible light photoredox conditions. Using these precursors, the first net redox-neutral coupling of tertiary and secondary alcohols with electron-deficient alkenes is achieved. ...[more]

PMID: 26322524

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Direct construction of quaternary carbons from tertiary alcohols via photoredox-catalyzed fragmentation of tert-alkyl N-phthalimidoyl oxalates.

Project description:A convenient method for the direct construction of quaternary carbons from tertiary alcohols by visible-light photoredox coupling of tert-alkyl N-phthalimidoyl oxalate intermediates with electron-deficient alkenes is reported.

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Visible light photoredox-catalyzed deoxygenation of alcohols.

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Fragment Coupling and the Construction of Quaternary Carbons Using Tertiary Radicals Generated From tert-Alkyl N-Phthalimidoyl Oxalates By Visible-Light Photocatalysis.

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Naphthalene diimides with improved solubility for visible light photoredox catalysis.

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Alcohol Etherification via Alkoxy Radicals Generated by Visible-Light Photoredox Catalysis.

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Oxydifluoromethylation of Alkenes by Photoredox Catalysis: Simple Synthesis of CF2H-Containing Alcohols.

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