期刊
TETRAHEDRON
卷 63, 期 32, 页码 7667-7672出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2007.05.029
关键词
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A mild method for the preparation of aryl and alkenylsulfones from the cross-coupling reaction of organoboronic acids and sodium sulfinate salts is described. Optimized conditions utilize a catalytic amount of copper( II) acetate monohydrate with 1,10-phenanthroline as ligand in the presence of 4 angstrom molecular sieves. A co-solvent mixture of dichloromethane/ DMSO was used, with reactions occurring at 40 degrees C under an atmosphere of oxygen. Reaction at room temperature also yields sulfone product, but in lower yields. The method tolerates a variety of substituents on the organoboronic acid, including amide, aldehyde, halide and nitro functionalities, as well as ortho-substituents. In general, the reaction is found to be less efficient using arylboronic acids bearing electron-withdrawing substituents, or using aryltrifluoroborate salts. (C) 2007 Elsevier Ltd. All rights reserved.
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