Ausbalancieren von C=C‐Funktionalisierung und C=O‐Reduktion in der Cu‐H‐Katalyse

Mohr, Jens; Oestreich, Martin

doi:10.1002/ange.201606701

Angewandte Chemie

2016

DOI: 10.1002/ange.201606701

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Ausbalancieren von C=C‐Funktionalisierung und C=O‐Reduktion in der Cu‐H‐Katalyse

Jens Mohr

Martin Oestreich

Abstract: Coppercabana: Es wurde gezeigt, dass die Kupfer(I)‐hydrid‐katalysierte Funktionalisierung nichtaktivierter Alkene mit konventioneller Carbonylreduktion kompatibel ist. Durch die Kombination beider Reaktionswege oder komplette Unterdrückung der C=O‐Reduktion zugunsten der C=C‐Funktionalisierung wurden Methoden für die stereoselektive Synthese einer Vielzahl chiraler Verbindungen entwickelt.

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Cited by 4 publications

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Cu‐Catalyzed Hydroxymethylation of Unactivated Alkyl Iodides with CO To Provide One‐Carbon‐Extended Alcohols

Zhao

Mankad

2018

Angewandte Chemie

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We have developed ar eductive carbonylation method by which unactivated alkyli odides can be hydroxymethylated to provideo ne-carbon-extended alcohol products under Cu-catalyzed conditions.The method is tolerant of alkyl b-hydrogen atoms,i sr obust towards aw ide variety of functional groups,a nd was applied to primary,s econdary,a nd tertiary alkyli odide substrates.M echanistic experiments indicate that the transformation proceeds by atom-transfer carbonylation (ATC) of the alkyli odide followed in tandem by two CuH-mediated reductions in rapid succession. This radical mechanism renders the Cu-catalyzed system complementary to precious-metal-catalyzed reductive carbonylation reactions.

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Cu‐Catalyzed Hydroxymethylation of Unactivated Alkyl Iodides with CO To Provide One‐Carbon‐Extended Alcohols

Zhao

Mankad

2018

Angewandte Chemie

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Cu‐Catalyzed Hydroxymethylation of Unactivated Alkyl Iodides with CO To Provide One‐Carbon‐Extended Alcohols

Zhao

Mankad

2018

Angew Chem Int Ed

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We have developed a reductive carbonylation method by which unactivated alkyl iodides can be hydroxymethylated to provide one-carbon-extended alcohol products under Cu-catalyzed conditions. The method is tolerant of alkyl β-hydrogen atoms, is robust towards a wide variety of functional groups, and was applied to primary, secondary, and tertiary alkyl iodide substrates. Mechanistic experiments indicate that the transformation proceeds by atom-transfer carbonylation (ATC) of the alkyl iodide followed in tandem by two CuH-mediated reductions in rapid succession. This radical mechanism renders the Cu-catalyzed system complementary to precious-metal-catalyzed reductive carbonylation reactions.

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Catalytic Generation and Chemoselective Transfer of Nucleophilic Hydrides from Dihydrogen

Pape

Brechmann

Teichert

2018

Chemistry A European J

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Copper(I)–N‐heterocyclic‐carbene (NHC) complexes enabled the catalytic generation of nucleophilic hydrides from dihydrogen (H2) and their subsequent transfer to allylic chlorides. The highly chemoselective catalyst displayed no concomitant hydrogenation reactivity; in fact, the terminal double bond formed in the hydride transfer remained intact. Switching to deuterium gas (D2) allowed for regioselective monodeuteration with excellent isotope incorporation.

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Ausbalancieren von C=C‐Funktionalisierung und C=O‐Reduktion in der Cu‐H‐Katalyse

Cited by 4 publications

References 17 publications

Cu‐Catalyzed Hydroxymethylation of Unactivated Alkyl Iodides with CO To Provide One‐Carbon‐Extended Alcohols

Cu‐Catalyzed Hydroxymethylation of Unactivated Alkyl Iodides with CO To Provide One‐Carbon‐Extended Alcohols

Cu‐Catalyzed Hydroxymethylation of Unactivated Alkyl Iodides with CO To Provide One‐Carbon‐Extended Alcohols

Catalytic Generation and Chemoselective Transfer of Nucleophilic Hydrides from Dihydrogen

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