Cobalt‐Catalyzed Reductive Coupling of Alkynes and Acrylates Bearing a Leaving Group: Construction of Cyclobutene Rings

Fujihara, Tetsuaki; Kukita, Susumu; Yagi, Yuki; Kirihara, Maho; Nogi, Keisuke; Tsuji, Yasushi

doi:10.1002/ajoc.201800561

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2022

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Cited by 3 publications

References 30 publications

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Carbocycles from Annulation of Alkynes and Alkenes

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Addition Reactions With Unsaturated Hydrocarbons

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Carbocycles from Annulation of Alkynes and Alkenes

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Addition Reactions With Unsaturated Hydrocarbons

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Selective Reductive Coupling of Vinyl Azaarenes and Alkynes via Photoredox Cobalt Dual Catalysis

Liu

et al. 2022

Angewandte Chemie

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A visible light-induced Co-catalyzed highly regio-and stereoselective reductive coupling of vinyl azaarenes and alkynes has been developed. Notably, Hünig's base together with simple ethanol has been successfully applied as the hydrogen sources instead of commonly used Hantzsch esters in this catalytic photoredox reaction. This approach has considerable advantages for the straightforward synthesis of stereodefined multiple substituted alkenes bearing an azaarene motif, such as excellent regioselectivity (> 20 : 1 for > 30 examples) and stereoselectivity (> 20 : 1 E/Z), broad substrate scope and good functional group compatibility under mild reaction conditions, which has been utilized in the concise synthesis of natural product monomorine I. A reasonable catalytic reaction pathway involving protolysis of the cobaltacyclopentene intermediate has been proposed based on the mechanistic studies.

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Selective Reductive Coupling of Vinyl Azaarenes and Alkynes via Photoredox Cobalt Dual Catalysis

Liu

et al. 2022

Angew Chem Int Ed

View full text Add to dashboard Cite

A visible light‐induced Co‐catalyzed highly regio‐ and stereoselective reductive coupling of vinyl azaarenes and alkynes has been developed. Notably, Hünig's base together with simple ethanol has been successfully applied as the hydrogen sources instead of commonly used Hantzsch esters in this catalytic photoredox reaction. This approach has considerable advantages for the straightforward synthesis of stereodefined multiple substituted alkenes bearing an azaarene motif, such as excellent regioselectivity (>20 : 1 for >30 examples) and stereoselectivity (>20 : 1 E/Z), broad substrate scope and good functional group compatibility under mild reaction conditions, which has been utilized in the concise synthesis of natural product monomorine I. A reasonable catalytic reaction pathway involving protolysis of the cobaltacyclopentene intermediate has been proposed based on the mechanistic studies.

show abstract

Cobalt‐Catalyzed Reductive Coupling of Alkynes and Acrylates Bearing a Leaving Group: Construction of Cyclobutene Rings

Cited by 3 publications

References 30 publications

Carbocycles from Annulation of Alkynes and Alkenes

Carbocycles from Annulation of Alkynes and Alkenes

Selective Reductive Coupling of Vinyl Azaarenes and Alkynes via Photoredox Cobalt Dual Catalysis

Selective Reductive Coupling of Vinyl Azaarenes and Alkynes via Photoredox Cobalt Dual Catalysis

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