Catalytic [2+2+1] Synthesis of Fused Thiophenes Using Thiocarbonyls as Sulfur Donors |
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| Authors: | Kazuma Matsui Dr. Masatoshi Shibuya Prof. Dr. Yoshihiko Yamamoto |
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| Affiliation: | Department of Basic Medicinal Sciences, Graduate School of Pharmaceutical Sciences, Nagoya University, Chikusa, Nagoya, Japan |
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| Abstract: | The use of N‐(p‐chlorophenyl)methylbenzoxazole‐2‐thione as a sulfur‐atom donor enables the catalytic [2+2+1] cycloaddition of diynes in wet DMF at 80 °C when open to air, thus affording diverse fused thiophenes with good yields and wide functional‐group compatibility. A plausible mechanism, involving a cationic ruthenacycle intermediate, was also proposed on the basis of several control experiments. |
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| Keywords: | alkynes cycloaddition reaction mechanisms ruthenium sulfur heterocycles |
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