A mild method for the replacement of a hydroxyl group by halogen. 1. Scope and chemoselectivity

作者：Munyemana Francois; George Isabelle; Devos Alain; Colens Alain; Badarau Eduard; Frisque He**ain Anne Marie; Loudet Aurore; Differding Edmond; Damien Jean Marie; Remion Jeanine; Van Uytbergen Jacqueline; Ghosez Leon^*

来源：Tetrahedron, 2016, 72(3): 420-430.

DOI：10.1016/j.tet.2015.11.060

• alpha-Haloenamines
• Alcohols
• Carboxylic acids
• Alkyl halides
• Acyl halides

alpha-Chloro-, bromo- and iodoenamines, which are readily prepared from the corresponding isobutyramides have been found to be excellent reagents for the transformation of a wide variety of alcohols or carboxylic acids into the corresponding halides. Yields are high and conditions are very mild thus allowing for the presence of sensitive functional groups. The reagents can be easily tuned allowing therefore the selective monohalogenation of polyhydroxylated molecules. The scope and chemoselectivity of the reactions have been studied and reaction mechanisms have been proposed.

• 出版日期2016-1-21