10.1002/chem.201805137
Chemistry - A European Journal
COMMUNICATION
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Acknowledgements
This work was generously supported by the Spanish Ministerio
de Economía y Competitividad (MINECO; grant no. CTQ2017-
88171-P), the Generalitat Valenciana (GV; grant no.
AICO/2017/007), and the Instituto de Síntesis Orgánica (ISO). I.
M.-G. thanks the Vicerrectorado de Investigación
Transferencia del Conocimiento of the Universidad de Alicante
for a pre-doctoral grant (no. UAFPU2016-034).
y
Keywords: C-C coupling • copper nanoparticles •
heterogeneous catalysis • nitrocompounds • nitrogen
heterocycles
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[16] The reaction of tetrahydroisoquinoline 2a with nitromethane led to the
typical
CDC
product,
i.e.,
1-(nitromethyl)-2-phenyl-1,2,3,4-
tetrahydroisoquinoline.
[17] The presence of nitrites or nitrates in the reaction crude can be ruled
out because of their negligible detected levels by ionic chromatography
(20 and 55 ng, respectively, in a 0.3 mmol scale reaction).
[18] Other oxidants were found to be less effective: Mn3O4, I2,
CuBr·SMe2/DABCO/O2, DDQ, CuCl/TEMPO. A thorough optimization
of the amount of MnO2 has not been conducted but an acceptable 80%
conversion into 6aa has been obtained with 10 mol% MnO2 after 1.5 h.
[7]
To the best of our knowledge (SciFinder), there are about 100
published articles reporting this transformation; ca. 650 reactions with
all type of nitroalkanes and ca. 200 reactions involving nitroalkanes
other than nitromethane.
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