研究了苄基卤代物与三丁基烯内基锡的偶联反应,当以10mol%Cu(OTf)2为催化剂,CH2Cl2为溶剂时,1-氯甲基-4-苯基萘与三丁基烯丙基锡于室温反应1 h,交叉偶联反应产物1-(3-丁烯基)-4-苯基萘(3b)收率即达93%.结果表明,芳环含供电子基的底物反应活性较高,在室温反应几分钟即可完成,而芳环含吸电子基的底物反应活性低.反应产物3b,1-溴-4-(3-丁烯基)萘(3c)和1-(3-丁烯基)-4-硝基萘(3f)未见报道,且其结构经表征确认.
Cross-coupling reaction of benzylic halides with allyltributylstannane was investigated. Desired cross-coupling products were obtained in satisfactory yields using Cu(OTf)2 as the catalyst. For example, cross-coupling product 1-(but-3-en-l-yl)-4-phenylnaphthalene (3b) was obtained in 93% yield when the reaction of 1-chloromethyl-4-phenylnaphthalene with allyltributylstannane was carried out in the presence of 10 mol% of Cu(OTf)2 in CH2C12 at room temperature for 1 h. The reaction of a substrate bearing an electron-donating group on the aromatic ring was completed in a few minutes, whereas the reaction ofa substrate having an electron-withdrawing group on the aromatic ring needed prolonged reaction time. 3b, 1-bromo-4-(but-3-en-l-yl)naphthalene (3c), and 1-(but-3-en-l-yl)-4-nitronaphthalene (3t) were unknown compounds and their structure was confirmed by 1H NMR, 13C NMR, IR, and HRMS.