Palladium-catalyzed/norbornene-mediated C-H activation/N-tosylhydrazone insertion reaction: a route to highly functionalized vinylarenes.
A straightforward method for the synthesis of highly functionalized vinylarenes through palladium-catalyzed, norbornene-mediated C-H activation/carbene migratory insertion is described. Extension to a one-pot procedure is also developed. Furthermore, this method can also be used to generate polysubstituted bicyclic molecules. The reaction proceeds under mild conditions to give the products in satisfactory yields using readily available starting materials. This is a Catellani-Lautens reaction that incorporates different types of coupling partners. Additionally, this reaction is the first to demonstrate the possibility of combining Pd-catalyzed insertion of diazo compounds and Pd-catalyzed C-H activation.
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (P.R. China), Fax: (0086) 931-8912582.
Ping-Xin
PX
Zhou
Lan
L
Zheng
Jun-Wei
JW
Ma
Yu-Ying
YY
Ye
Xue-Yuan
XY
Liu
Peng-Fei
PF
Xu
Yong-Min
YM
Liang
CC coupling; CH activation; diazo compounds; palladium; synthetic methods