Cu(I)-Catalyzed Synthesis of Furan-Substituted Allenes by Use of Conjugated Ene-yne Ketones as Carbene Precursors

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• 作者：Fangdong Hu ; Ying Xia ; Chen Ma ; Yan Zhang ; Jianbo Wang
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：April 15, 2016
• 年：2016
• 卷：81
• 期：8
• 页码：3275-3285
• 全文大小：478K
• 年卷期：0
• ISSN：1520-6904

文摘

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.