Abstract
Both 1-arylalk-3-en-1-ynes and alka-1,5-dien-3-ynes have been synthesized under extremely mild reaction conditions in good to high yields via a sequential Suzuki-type and Sonogashira reaction in a one-pot manner. Thus, the protocol involves Cu-mediated cross-coupling reaction of (E )- or (Z )-alkenyldisiamylborane with (trimethylsilyl)ethynyl bromide in the presence of 1 M NaOMe and Pd/Cu-catalyzed cross-coupling reaction with aryl or alkenyl iodide in the presence of aqueous n -Bu4 NOH. The reaction with aryl iodide is tolerant of a wide variety of functional groups on the aromatic ring and leads to the stereoselective formation of (E )- and (Z )-1-arylalk-3-en-1-ynes. In addition, the reactions with (E )- and (Z )-1-iodoalk-1-enes have accomplished the construction of all possible combinations of geometrical isomers, (E ,E )-, (Z ,E )-, (E ,Z )-, and (Z ,Z )- alka-1,5-dien-3-ynes.
Key words
alkenylborane - (trimethylsilyl)ethynyl bromide - cross-coupling - 1-arylalk-3-en-1-yne - alka-1,5-dien-3-yne
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