State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116023, China.
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan.
J Org Chem. 2020 Jul 2;85(13):8740-8748. doi: 10.1021/acs.joc.0c01102. Epub 2020 Jun 15.
A method for the chemo-, regio-, and stereoselective one-pot synthesis of 1,3-enynes is described. The reaction of 2-chloro--(quinolin-8-yl)acetamides with terminal alkynes proceeds smoothly in the presence of a copper catalyst at room temperature to produce ()-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 ()-1,3-enynes.
描述了一种用于化学选择性、区域选择性和立体选择性一锅合成 1,3-烯炔的方法。在室温下，2-氯-（8-喹啉基）乙酰胺与末端炔烃在铜催化剂的存在下反应顺利进行，以令人满意至优异的收率得到（）-1,3-烯炔。机理研究表明，原位生成的内炔烃与末端炔烃的交叉二聚反应通过丙二烯中间体进行。导向基团 8-氨基喹啉在（）-1,3-烯炔的选择性合成中起着关键作用。
