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Catalytic [2+2+1] Synthesis of Fused Thiophenes Using Thiocarbonyls as Sulfur Donors
Author(s) -
Matsui Kazuma,
Shibuya Masatoshi,
Yamamoto Yoshihiko
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201609545
Subject(s) - sulfur , cationic polymerization , cycloaddition , catalysis , chemistry , compatibility (geochemistry) , combinatorial chemistry , organic chemistry , materials science , composite material
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.