Bromide as the Directing Group for β-Arylation of Thiophenes

Journal Article · 28 June 2022 · Synthesis

DOI: https://doi.org/10.1055/a-1838-8958 · OSTI ID:1885340

Zhang, Hong-Hai  ^[1]; Wang, Cai-Xia ^[1]; Sheng, Fei-Fei ^[1]; Liu, Kai-Hui ^[1]; Gu, Jian-Guo ^[1]; Shen, Kang ^[1]; Sun, Zheng-Yi ^[1]; Hong, Kunlun  ^[2]

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1. Nanjing Tech University (China)
2. Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)

Direct β-arylation of thiophene derivatives with bromide as directing group is disclosed. The reaction is conducted with PdCl₂/(p-tolyl)₃P as catalyst, silver carbonate as additive, and aryl iodide as coupling partner, affording brominated biaryl compounds as product. Control experiments indicated that the presence of bromide group enhances the reactivity of the C–H bond, enabling β-arylation. Additionally, the C–Br bond can be easily converted into many useful functional groups through a wide range of methodologies. The mechanistic study suggests that silver salt plays a key role in the C–H bond-activation step.

• Research Organization: Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Center for Nanophase Materials Sciences (CNMS)
• Sponsoring Organization: USDOE Office of Science (SC), Biological and Environmental Research (BER); National Natural Science Foundation of China (NSFC)
• Grant/Contract Number: AC05-00OR22725
• OSTI ID: 1885340
• Journal Information: Synthesis, Journal Name: Synthesis Journal Issue: 18 Vol. 54; ISSN 0039-7881
• Publisher: ThiemeCopyright Statement
• Country of Publication: United States
• Language: English