About the reaction of aryl fluorides with sodium sulfide: investigation into the selectivity of substitution of fluorobenzonitriles to yield mercaptobenzonitriles via SNAr displacement of fluorine

作者：Taldone Tony^*; Patel Pallav D; Patel Hardik J; Chiosis Gabriela

来源：Tetrahedron Letters, 2012, 53(20): 2548-2551.

DOI：10.1016/j.tetlet.2012.03.032

• Mercaptobenzonitrile
• Aryl fluoride
• SNAr
• Selectivity
• Sodium sulfide

In this report we describe a simple synthesis of mercaptobenzonitriles from the reaction of fluorobenzonitriles with Na2S in DMF at room temperature and following direct treatment with Zn/HCl. Significantly, 2- and 4-fluorobenzonitriles substituted with chlorine or bromine, from the reaction of but not iodine, undergo selective substitution of fluorine at room temperature to yield synthetically useful halo-substituted mercaptobenzonitriles.

• 出版日期2012-5-16