Efficient synthesis of carbazoles via PtCl2-catalyzed RT cyclization of 1-(indol-2-yl)-2,3-allenols: scope and mechanism.
A detailed study on the scope of the efficient PtCl(2)-catalyzed synthesis of carbazoles from 1-(indol-2-yl)-2,3-allenols is described. Through isotopic labeling experiments, it is confirmed that the reaction proceeds through a unique metal carbene intermediate, which undergoes subsequent highly selective 1,2-hydrogen migration to afford carbazoles. The reaction shows wide scope and allows the introduction of a variety of different substituents at different positions on the carbazole due to the substituent-loading capability of both indole and the allene moiety.
Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang, People's Republic of China.
Wangqing
W
Kong
Chunling
C
Fu
Shengming
S
Ma
D000466:Alkadienes / Q000737:chemistry; D002227:Carbazoles / Q000138:chemical synthesis*; D003500:Cyclization; D007211:Indoles / Q000737:chemistry*; D017671:Platinum Compounds / Q000737:chemistry*
D000466:Alkadienes; D002227:Carbazoles; D007211:Indoles; D017671:Platinum Compounds; C030173:platinum chloride; C025947:propadiene