Regio- and stereoselective cross-coupling of tert-propargyl alcohols with bis(trimethylsilyl)acetylene and its utilization in constructing a fluorescent donor-acceptor system |
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| Authors: | Horita Akinobu Tsurugi Hayato Funayama Atsushi Satoh Tetsuya Miura Masahiro |
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| Affiliation: | Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan. |
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| Abstract: | ![]()
1,1-Disubstituted 3-aryl-2-propyn-1-ols undergo regio- and stereoselective cross-coupling on treatment with bis(trimethylsilyl)acetylene in the presence of a rhodium catalyst via cleavage of C(sp)-C(sp3) and C(sp)-Si bonds to produce the corresponding 2-hydroxymethyl-(E)-enynes. The subsequent desilylative Sonogashira coupling followed by base-promoted cyclization affords fluorescent dihydrofuran derivatives. |
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