Open AccessNickel-catalysed retro-hydroamidocarbonylation of aliphatic amides to olefins
Author(s) -
Jiefeng Hu,
Minyan Wang,
Xinghui Pu,
Zhuangzhi Shi
Publication year - 2017
Publication title -
nature communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.559
H-Index - 365
ISSN - 2041-1723
DOI - 10.1038/ncomms14993
Subject(s) - amide , catalysis , chemistry , combinatorial chemistry , bond cleavage , reactivity (psychology) , functional group , organic chemistry , medicine , polymer , alternative medicine , pathology
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.