TY - JOUR
T1 - Copper-mediated reduction of azides under seemingly oxidising conditions: Catalytic and computational studies
AU - Zelenay, Benjamin
AU - Besora, Maria
AU - Monasterio, Zaira
AU - Ventura-Espinosa, David
AU - White, Andrew J.P.
AU - Maseras, Feliu
AU - Díez-González, Silvia
PY - 2018/1/1
Y1 - 2018/1/1
N2 - © The Royal Society of Chemistry 2018. The reduction of aryl azides in the absence of an obvious reducing agent is reported. Careful catalyst design led to the production of anilines in the presence of water and air. The reaction medium (toluene/water) is crucial for the success of the reaction, as DFT calculations support the formation of benzyl alcohol as the oxidation product. A singular catalytic cycle is presented for this transformation based on four key steps: nitrene formation through nitrogen extrusion, formal oxidative addition of water, C(sp3)-H activation of toluene and reductive elimination.
AB - © The Royal Society of Chemistry 2018. The reduction of aryl azides in the absence of an obvious reducing agent is reported. Careful catalyst design led to the production of anilines in the presence of water and air. The reaction medium (toluene/water) is crucial for the success of the reaction, as DFT calculations support the formation of benzyl alcohol as the oxidation product. A singular catalytic cycle is presented for this transformation based on four key steps: nitrene formation through nitrogen extrusion, formal oxidative addition of water, C(sp3)-H activation of toluene and reductive elimination.
U2 - 10.1039/c8cy00515j
DO - 10.1039/c8cy00515j
M3 - Article
VL - 8
SP - 5763
EP - 5773
JO - Catalysis Science and Technology
JF - Catalysis Science and Technology
SN - 2044-4753
IS - 22
ER -