Cu(OTf)_2催化苄基卤代物与三丁基烯丙基锡的偶联反应  

Cross-Coupling Reaction of Benzylic Halides with Allyltributylstannane Catalyzed by Cu(OTf)_2

作　　者：于晓强[1] 马永洁[1] 赵自然[2] 许占威[1] 包明[1] 

机构地区：[1]大连理工大学精细化工国家重点实验室,辽宁大连116012 [2]吉林大学第一医院整形外科,吉林长春130021

出　　处：《催化学报》2011年第3期472-476,共5页

基　　金：国家自然科学基金(21002010);高等学校博士学科点专项科研基金(20090041110012)

摘　　要：研究了苄基卤代物与三丁基烯丙基锡的偶联反应,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1h,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.

关 键 词：苄基卤代物 三丁基烯丙基锡 三氟甲基磺酸铜 偶联反应 

分 类 号：O643.32[理学—物理化学]