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  4. Rh(I)-Catalyzed Hydroamidation of Olefins via Selective Activation of N–H Bonds in Aliphatic Amines
 
research article

Rh(I)-Catalyzed Hydroamidation of Olefins via Selective Activation of N–H Bonds in Aliphatic Amines

Dong, Kaiwu
•
Fang, Xianjie
•
Jackstell, Ralf
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2015
Journal of the American Chemical Society

Hydroamidation of olefins constitutes an ideal, atom-efficient method to prepare carboxylic amides from easily available olefins, CO, and amines. So far, aliphatic amines are not suitable for these transformations. Here, we present a ligand- and additive-free Rh(I) catalyst as solution to this problem. Various amides are obtained in good yields and excellent regioselectivities. Notably, chemoselective amidation of aliphatic amines takes place in the presence of aromatic amines and alcohols. Mechanistic studies reveal the presence of Rh-acyl species as crucial intermediates for the selectivity and rate-limiting step in the proposed Rh(I)-catalytic cycle.

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Type
research article
DOI
10.1021/jacs.5b02218
Web of Science ID

WOS:000354910500032

Author(s)
Dong, Kaiwu
Fang, Xianjie
Jackstell, Ralf
Laurenczy, Gabor  
Li, Yuehui
Beller, Matthias
Date Issued

2015

Publisher

Amer Chemical Soc

Published in
Journal of the American Chemical Society
Volume

137

Issue

18

Start page

6053

End page

6058

Editorial or Peer reviewed

REVIEWED

Written at

OTHER

EPFL units
LCOM  
Available on Infoscience
May 26, 2015
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/114044
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