Rh-catalyzed Negishi alkyl-aryl cross-coupling leading to alpha- or beta-phosphoryl-substituted alkylarenes.
The catalytic cross-coupling between ArZnX and ICH(2)(CH(2))(n)P(O)(OEt)(2) (n = 0-3) has been investigated to determine the utility of the Rh catalyst during the alkyl-aryl cross-coupling and to develop a new synthetic method for phosphoryl-substituted alkylarenes. Rh-dppf exhibits an excellent catalytic activity for the reaction with the alkylphosphonate of n = 1, whereas for the reaction with those of n = 2 or 3, beta-hydride elimination mainly takes place. As for the reaction with an alkylphosphonate of n = 0, a polarity inversion of the coupling components is necessary in order to provide the coupling products; the phosphoryl analogue of the Reformatsky reagent and ArI give the cross-coupling products in good yields through the catalysis by Rh-dppf.
Takahashi
Hideki
H
Department of Chemistry, Faculty of Science, Okayama University, Tsushima, Okayama 700-8530, Japan.
Inagaki
Shinya
S
Yoshii
Naoko
N
Gao
Fuxing
F
Nishihara
Yasushi
Y
Takagi
Kentaro
K