Programmed synthesis of tetraarylthiophenes through sequential C-H arylation.
A general protocol for the programmed synthesis of tetraarylthiophenes has been established. The utilization of three catalysts, RhCl(CO){P[OCH(CF(3))(2)](3)}(2), PdCl(2)/P[OCH(CF(3))(2)](3), and PdCl(2)/bipy, enables regioselective sequential arylations at the three C-H bonds of 3-methoxythiophene with iodoarenes. Interesting metal- and ligand-controlled regiodivergent C-H arylations have been uncovered during this study. The installation of fourth aryl groups to the thus-generated 2,4,5-triaryl-3-methoxythiophenes has been accomplished through a sequence of demethylation, triflation, and Suzuki-Miyaura coupling.
Yanagisawa
Shuichi
S
Department of Chemistry, Graduate School of Science, Nagoya University, Nagoya 464-8602, Japan.
Ueda
Kirika
K
Sekizawa
Hiromi
H
Itami
Kenichiro
K
D002244:Carbon / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry*
D013876:Thiophenes; D002244:Carbon; D006859:Hydrogen; D010100:Oxygen