Premium
Rhodaelectrocatalysis for Annulative C−H Activation: Polycyclic Aromatic Hydrocarbons through Versatile Double Electrocatalysis
Author(s) -
Kong WeiJun,
Finger Lars H.,
Oliveira João C. A.,
Ackermann Lutz
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201901565
Subject(s) - chemistry , electrocatalyst , combinatorial chemistry , alkyne , catalysis , organic chemistry , electrochemistry , electrode
Rapid access to structurally diversified polycyclic aromatic hydrocarbons (PAHs) in a controlled manner is of key significance in materials sciences. Herein, we describe a strategy featuring two distinct electrocatalytic C−H transformations for the synthesis of novel nonplanar PAHs. The combination of rhodaelectrooxidative C−H activation/[2+2+2] alkyne annulation of easily accessible boronic acids with electrocatalytic cyclodehydrogenation provided modular access to diversely substituted PAHs with electricity as a sustainable oxidant. The unique molecular topology as well as the photophysical and electronic properties of the thus obtained PAHs were fully analyzed. The unique power of this metallaelectrocatalysis method was demonstrated by the chemoselective assembly of synthetically useful iodo‐substituted PAHs.