Synthesis
General procedure for the synthesis of 4-N,N-dimethylaminoiodobenzene from N,N-dimethylaniline: to a stirred solution of N,N-dimethylaniline (1 mmol) in dichloromethane (CH2Cl2) or 1,2-dichloroethane ((CH2Cl)2) (0.1 M) was added sequentially Ph3PAuNTf2 (0.025 mmol, 19 mg; if using the 2:1 complex of Ph3PAuNTf2 with toluene) and N-iodosuccinimide (NIS, 1.1 mmol, 248 mg). The reaction mixture was stirred at room temperature or reacted under reflux conditions until complete conversion of the feedstock was shown by thin layer chromatography (TLC) monitoring. Upon completion of the reaction, the solvent was evaporated under reduced pressure and the resulting crude product was purified by fast column chromatography using different ratios of hexane and ethyl acetate (EtOAc) as eluents, resulting in pure 4-N,N-dimethylaminoiodobenzene.
References
[1] RSC Advances, 2014, vol. 4, # 12, p. 6267 - 6274
[2] Journal of Organic Chemistry, 1993, vol. 58, # 8, p. 2058 - 2060
[3] Tetrahedron Letters, 2005, vol. 46, # 32, p. 5421 - 5423
[4] Tetrahedron, 2005, vol. 61, # 49, p. 11657 - 11663
[5] Helvetica Chimica Acta, 2007, vol. 90, # 11, p. 2087 - 2095
