TY - JOUR
T1 - Divergent Carbocatalytic Routes in Oxidative Coupling of Benzofused Heteroaryl Dimers
T2 - A Mechanistic Update
AU - Casadio, David S.
AU - Aikonen, Santeri
AU - Lenarda, Anna
AU - Nieger, Martin
AU - Hu, Tao
AU - Taubert, Stefan
AU - Sundholm, Dage
AU - Muuronen, Mikko
AU - Wirtanen, Tom
AU - Helaja, Juho
PY - 2021/3/17
Y1 - 2021/3/17
N2 - Mildly thermally air or HNO3 oxidized activated carbons catalyse oxidative dehydrogenative couplings of benzo[b]fused heteroaryl 2,2’‐dimers, e.g., 2‐(benzofuran‐2‐yl)‐1 H‐indole, to chiral 3,3’‐coupled cyclooctatetraenes or carbazole‐type migrative products under O2 atmosphere. DFT calculations show that the radical cation and the Scholl‐type arenium cation mechanisms lead to different products with 2‐(benzofuran‐2‐yl)‐1H‐indole, being in accordance with experimental product distributions.
AB - Mildly thermally air or HNO3 oxidized activated carbons catalyse oxidative dehydrogenative couplings of benzo[b]fused heteroaryl 2,2’‐dimers, e.g., 2‐(benzofuran‐2‐yl)‐1 H‐indole, to chiral 3,3’‐coupled cyclooctatetraenes or carbazole‐type migrative products under O2 atmosphere. DFT calculations show that the radical cation and the Scholl‐type arenium cation mechanisms lead to different products with 2‐(benzofuran‐2‐yl)‐1H‐indole, being in accordance with experimental product distributions.
KW - C coupling
KW - C−
KW - cyclooctatetraene
KW - density functional calculations
KW - heterogeneous catalysis
KW - oxidative dehydrogenative coupling
KW - 116 Chemical sciences
U2 - 10.1002/chem.202005433
DO - 10.1002/chem.202005433
M3 - Article
SN - 0947-6539
VL - 27
SP - 5283
EP - 5291
JO - Chemistry: A European Journal
JF - Chemistry: A European Journal
IS - 16
ER -