CuI-Catalyzed Coupling Reactions of Aryl Iodides and Bromides with Thiols Promoted by Amino Acid Ligands

Wei Deng; Yan Zou; Ye-Feng Wang; Lei Liu; Qing-Xiang Guo

doi:10.1055/s-2004-825584

LETTER

CuI-Catalyzed Coupling Reactions of Aryl Iodides and Bromides with Thiols Promoted by Amino Acid Ligands

Wei Deng, Yan Zou, Ye-Feng Wang, Lei Liu*, Qing-Xiang Guo*
Deparment of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. China
e-Mail: leiliu@chem.columbia.edu; e-Mail: qxguo@ustc.edu.cn;

Abstract

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Abstract

Novel mild conditions for the CuI-catalyzed coupling reactions of aryl iodides and bromides with aliphatic and aromatic thiols using amino acids as the ligand are reported.

Key words

copper iodide - aryl sulfide - cross-coupling - amino acid ligand

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References

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All the products are known compounds except for 1,4-bis(octylthio)benzene.

1,4-Bis(octylthio)benzene: White solid. IR: 2954, 2921, 1465, 1113, 803 cm^-1. ¹H NMR (CDCl₃, 300 MHz): δ = 7.23 (s, 4 H), 2.88 (t, J = 7.3 Hz, 4 H), 1.63 (m, J = 6.8 Hz, 4 H), 1.40-1.26 (br m, 20 H), 0.88 (t, J = 6.4 Hz, 6 H). ¹³C NMR (300 MHz, CDCl₃): δ = 134.6, 129.8, 34.2, 32.0, 29.32, 29.29, 29.0, 22.8, 14.2. MS (EI): m/z (relative intensity): 366 (100), 254 (25), 142 (35). Anal. Calcd for C₂₂H₃₈S₂: C, 72.06; H, 10.46. Found: C, 72.20; H, 10.58.