Rhodium-catalyzed anti selective cross-addition of bis(trimethylsilyl)acetylene to diarylacetylenes via carbon-silicon bond cleavage.
The addition of bis(trimethylsilyl)acetylene to diarylacetylenes proceeds efficiently and selectively in a formal anti fashion in the presence of [Rh(OH)(cod)]2/bisphosphine and phenol as catalyst and activator, respectively, accompanied by cleavage of one of the C-Si bonds to produce the corresponding (Z)-enynes. The products can further couple with the same or a different diarylacetylene molecule to give rise to (Z,Z)-1,2,5,6-tetraaryl-1,5-hexadien-3-ynes that show relatively strong solid-state fluorescence.
Horita
Akinobu
A
Department of Applied Chemistry, Faculty of Engineering, Osaka University, Osaka, Japan.
Tsurugi
Hayato
H
Satoh
Tetsuya
T
Miura
Masahiro
M