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Nickel-catalysed retro-hydroamidocarbonylation of aliphatic amides to olefins.

ABSTRACT: Amide and olefins are important synthetic intermediates with complementary reactivity which play a key role in the construction of natural products, pharmaceuticals and manmade materials. Converting the normally highly stable aliphatic amides into olefins directly is a challenging task. Here we show that a Ni/NHC-catalytic system has been established for decarbonylative elimination of aliphatic amides to generate various olefins via C-N and C-C bond cleavage. This study not only overcomes the acyl C-N bond activation in aliphatic amides, but also encompasses distinct chemical advances on a new type of elimination reaction called retro-hydroamidocarbonylation. This transformation shows good functional group compatibility and can serve as a powerful synthetic tool for late-stage olefination of amide groups in complex compounds.

SUBMITTER: Hu J

PROVIDER: S-EPMC5424121 | biostudies-literature | 2017 May

REPOSITORIES: biostudies-literature

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Nickel-catalysed retro-hydroamidocarbonylation of aliphatic amides to olefins.

Hu Jiefeng J Wang Minyan M Pu Xinghui X Shi Zhuangzhi Z

Nature communications 20170505

Amide and olefins are important synthetic intermediates with complementary reactivity which play a key role in the construction of natural products, pharmaceuticals and manmade materials. Converting the normally highly stable aliphatic amides into olefins directly is a challenging task. Here we show that a Ni/NHC-catalytic system has been established for decarbonylative elimination of aliphatic amides to generate various olefins via C-N and C-C bond cleavage. This study not only overcomes the ac ...[more]

PMID: 28474671

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