Catalytic [2+2+1] Synthesis of Fused Thiophenes Using Thiocarbonyls as Sulfur Donors. Issue 49 (11th November 2016)

• Record Type: Journal Article
• Authors: Matsui, Kazuma; Shibuya, Masatoshi; Yamamoto, Yoshihiko
• Is Part Of: Angewandte Chemie international edition. Volume 55:Issue 49(2016)
• Page Start: 15397
• Page End: 15400
• Publication Date: 2016-11-11
• Subjects: alkynes -- cycloaddition -- reaction mechanisms -- ruthenium -- sulfur heterocycles; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201609545
• Languages: English
• ISSNs: 1433-7851

Abstract

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. 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 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.