Abstract
A method for the chemo-, regio-, and stereoselective one-pot synthesis of 1,3-enynes is described. The reaction of 2-chloro-N-(quinolin-8-yl)acetamides with terminal alkynes proceeds smoothly in the presence of a copper catalyst at room temperature to produce (E)-1,3-enynes in satisfactory to excellent yields. The mechanism study reveals that the cross-dimerization of internal alkynes generated in situ with terminal alkynes proceeds via allene intermediates. The directing group 8-aminoquinoline plays a key role in the current selective synthesis of (E)-1,3-enynes.
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