TY - JOUR
T1 - Microwave-assisted efficient one-pot synthesis of 9-phenyl-9,10- disilatriptycene and its bridgehead functionalization
AU - Kuribara, Takayoshi
AU - Ishida, Shintaro
AU - Kudo, Takako
AU - Kyushin, Soichiro
PY - 2013/4/8
Y1 - 2013/4/8
N2 - 9-Phenyl-9,10-disilatriptycene (2) was synthesized by the reaction of bis(2-bromophenyl)silane (1) with magnesium in THF. On conventional heating, 2 and cis-9,10-diphenyl-9,10-dihydro-9,10-disilaanthracene (cis-3) were obtained in 31% and 36% yields, respectively. However, the yield of 2 was significantly increased to 71% on microwave irradiation. Theoretical calculations suggest that the intermediary Grignard reagents generated from trans- and cis-9,10-diaryl-9,10-dihydro-9,10-disilaanthracenes have quite different reactivity for construction of the 9,10-disilatriptycene skeleton. The bridgehead Si-H moiety of 2 was readily functionalized to give several 9,10-disilatriptycene derivatives.
AB - 9-Phenyl-9,10-disilatriptycene (2) was synthesized by the reaction of bis(2-bromophenyl)silane (1) with magnesium in THF. On conventional heating, 2 and cis-9,10-diphenyl-9,10-dihydro-9,10-disilaanthracene (cis-3) were obtained in 31% and 36% yields, respectively. However, the yield of 2 was significantly increased to 71% on microwave irradiation. Theoretical calculations suggest that the intermediary Grignard reagents generated from trans- and cis-9,10-diaryl-9,10-dihydro-9,10-disilaanthracenes have quite different reactivity for construction of the 9,10-disilatriptycene skeleton. The bridgehead Si-H moiety of 2 was readily functionalized to give several 9,10-disilatriptycene derivatives.
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U2 - 10.1021/om301170r
DO - 10.1021/om301170r
M3 - Article
AN - SCOPUS:84876010144
VL - 32
SP - 2092
EP - 2098
JO - Organometallics
JF - Organometallics
SN - 0276-7333
IS - 7
ER -