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– The reaction of 3-hexylthiophene with Knochel-Hauser base (TMPMgCl·LiCl) induced the metalation at the 5-position of the thiophene ring selectively. Following addition of several aryl halides in the presence of a nickel or palladium catalyst afforded regioselectively arylated thiophene in good to excellent yields. INTRODUCTION CH functionalization of heteroaromatic compounds recently attracts much attention 1,2 since a variety of organic compounds bearing heteroaromatic moiety in the structure are found in a wide range of advanced organic materials 3 as well as biologically active molecules. 4 Therefore, development of a practical synthetic strategy for such molecules is an important issue in organic synthesis. We have been engaged in the development of synthetic methodologies to afford functionalized heteroaromotics via transition metal catalyzed CH functionalization. 5 Several functionalization reactions, which take place at a carbon atom of an electron-deficient 6 and enriched |
