5 years ago

CuI/Oxalic Diamide-Catalyzed Cross-Coupling of Thiols with Aryl Bromides and Chlorides

CuI/Oxalic Diamide-Catalyzed Cross-Coupling of Thiols with Aryl Bromides and Chlorides
Chin-Fa Lee, Bo-Hao Shih, Kai Du, Daggula Mallikarjuna Reddy, Yung-Jing Xue, Yi-Ling Chen, Chao-En Li, Chia-Wei Chen
We report a general copper-catalyzed cross-coupling of thiols with aryl halides by using N-aryl-N′-alkyl oxalic diamide (L3) or N,N′-dialkyl oxalic diamide (L5) as the ligand. Both aryl and alkyl thiols can be coupled with unactivated aryl bromides and chlorides to give the desired products in good yields. Furthermore, this system features a broad substrate scope and good tolerance of functional groups. Importantly, the oxalic diamides are stable and can be prepared easily from commercially available and cheap starting materials. A practical synthetic method for diversified thioethers using oxalic diamides as highly air-stable ligands through copper catalysis is demonstrated. A variety of aryl- and alkyl thiols can be coupled with aryl bromides and chlorides to afford the corresponding thioethers in good yields. This work is the first general method for copper-catalyzed thioetherification of unactivated aryl chlorides.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201701671

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