title: Cu(I)-Catalyzed Synthesis of Furan-Substituted Allenes by Use of Conjugated Ene-yne Ketones as Carbene Precursors.
abstract: 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 organocopper species. The organocopper species thus generated can be trapped by proton or allyl halide, affording tri- or tetrasubstituted allenes, respectively. The reaction, which is characterized by its mild reaction conditions and the utilization of cheap copper(I) iodide as catalyst, allows for synthesis of a variety of furan-substituted allenes with a wide range of functional groups tolerance.
authors.affiliation: Beijing National Laboratory of Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University , Beijing 100871, China.
authors.forename: Fangdong
authors.initials: F
authors.lastname: Hu
authors.affiliation: Beijing National Laboratory of Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University , Beijing 100871, China.
authors.forename: Ying
authors.initials: Y
authors.lastname: Xia
authors.affiliation: School of Chemistry and Chemical Engineering, Shandong University , Jinan 250100, China.
authors.forename: Chen
authors.initials: C
authors.lastname: Ma
authors.affiliation: Beijing National Laboratory of Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University , Beijing 100871, China.
authors.forename: Yan
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: Beijing National Laboratory of Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University , Beijing 100871, China.
authors.forename: Jianbo
authors.initials: J
authors.lastname: Wang