A novel palladium-catalyzed interannular selective C-H silylation of 1,1′-biaryl-2-acetamides is described. The combination of palladium catalyst with copper oxidant enables meta- or ortho-selective C-H silylation by employing hexamethyldisilane as a trimethylsilyl source, which relies on the control of NBE derivatives as a switch, thus providing straightforward access to divergent silicon-containing 1,1′-biaryl-2-acetamides.
Ruthenium-catalyzed ortho-arylation of acetanilides with aromatic boronic acids: An easy route to prepare phenanthridines and carbazoles
The highly regioselective ortho-arylation of acetanilides with aromatic boronic acids in the presence of a Ru(ii) complex (3 mol%), AgSbF6 (12 mol%), Cu(OTf)2 (20 mol%) and Ag2O (1.0 eq.) is described. Later, ortho-arylated acetanilides were converted into phenanthridine and carbazole derivatives by using Ph3PO and Tf2O or palladium or Cu(OTf)2 catalysts.
Chinnagolla, Ravi Kiran,Jeganmohan, Masilamani
supporting information
p. 2442 - 2444
(2014/03/21)
Highly effective Pd-catalyzed ortho olefination of acetanilides: Broad substrate scope and high tolerability
Bring it on! An effective Pd-catalyzed ortho olefination of various acetanilides has been developed. This transformation has a broad substrate scope and wide functional-group tolerability, regardless of the electronic and steric properties of acetanilide substrates, providing a straightforward access to highly functionalized arenes.
Kim, Byung Seok,Jang, Chungsik,Lee, Dong Jin,Youn, So Won
p. 2336 - 2340
(2011/06/25)
A synthetic approach to carbazoles using electrochemically generated hypervalent iodine oxidant
Carbazoles were successfully synthesized by oxidative cyclization of the corresponding diaryl derivatives using electrochemically generated hypervalent iodine oxidant. Electron-withdrawing nitro and donating methoxy groups at the para position of the acetamide group interfered with cyclization. Glycozoline (8) was successfully synthesized in five steps with 50% overall yield.