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Base Metal-Catalyzed Direct Olefinations of Alcohols with Sulfones.

ABSTRACT: Herein, a base-metal nickel-catalyzed direct olefination of alcohols with sulfones is reported. The reaction operates under low catalyst loading and does not require an external redox reagent. A wide range of trans-stilbenes and styrenes were synthesized in good yields and selectivities. Biologically active stilbene DMU-212 could also be synthesized in a single step under these conditions. Mechanistic studies involving kinetic isotope effect, deuterium labeling experiments, and catalytic and stoichiometric reactions with possible catalytic intermediates were performed to elucidate a plausible mechanism.

SUBMITTER: Waiba S

PROVIDER: S-EPMC6648817 | biostudies-literature | 2019 Apr

REPOSITORIES: biostudies-literature

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Base Metal-Catalyzed Direct Olefinations of Alcohols with Sulfones.

Waiba Satyadeep S Das Animesh A Barman Milan K MK Maji Biplab B

ACS omega 20190418 4

Herein, a base-metal nickel-catalyzed direct olefination of alcohols with sulfones is reported. The reaction operates under low catalyst loading and does not require an external redox reagent. A wide range of <i>trans</i>-stilbenes and styrenes were synthesized in good yields and selectivities. Biologically active stilbene <b>DMU-212</b> could also be synthesized in a single step under these conditions. Mechanistic studies involving kinetic isotope effect, deuterium labeling experiments, and cat ...[more]

PMID: 31459819

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