标题：Cu(I)-Catalyzed Synthesis of Furan-Substituted Allenes by Use of Conjugated Ene-yne Ketones as Carbene Precursors
作者：Hu, Fangdong; Xia, Ying; Ma, Chen; Zhang, Yan; Wang, Jianbo
作者机构：[Hu, Fangdong; Xia, Ying; Zhang, Yan; Wang, Jianbo] Peking Univ, Beijing Natl Lab Mol Sci, Key Lab Bioorgan Chem & Mol Engn, Minist Educ,Coll Chem, Be 更多
通讯作者地址：[Wang, JB]Peking Univ, Beijing Natl Lab Mol Sci, Key Lab Bioorgan Chem & Mol Engn, Minist Educ,Coll Chem, Beijing 100871, Peoples R China.
来源：JOURNAL OF ORGANIC CHEMISTRY
摘要：The synthesis of furan-substituted allenes using conjugated ene-yne ketones as carbene source has been developed. For this reaction, bases play vital roles in controlling the reaction pathways, allowing for access to two types of allene products through trapping of different electrophiles. Mechanistically, the catalytic procedure generated a Cu(I) (2-furyl)carbene intermediate, which is subsequently followed by a migratory insertion process to afford nucleophilic organo copper species. The organocopper species thus generated can be trapped by proton or ally! halide, affording tri- or tetrasubstituted allenes, respectively. The reaction, which is characterized by its mild reaction conditions and the utilization of cheap copper(1) iodide as catalyst, allows for synthesis of a variety of furan-substituted allenes with a wide range of functional groups tolerance.