镍催化的带有8-氨基喹啉导向基团的烯烃的还原1,2-二炔基化反应
Nickel-Catalyzed Reductive 1,2-Dialkynylation of Alkenes Bearing an 8-Aminoquinoline Directing Group.
作者信息
Pan Rui, Shi Cong, Zhang Dongquan, Tian Yang, Guo Songjin, Yao Hequan, Lin Aijun
机构信息
State Key Laboratory of Natural Medicines (SKLNM) and Department of Medicinal Chemistry, School of Pharmacy , China Pharmaceutical University , Nanjing 210009 , P. R. China.
出版信息
Org Lett. 2019 Nov 15;21(22):8915-8920. doi: 10.1021/acs.orglett.9b03147. Epub 2019 Nov 5.
An unprecedented nickel-catalyzed reductive 1,2-dialkynylation of alkenes bearing an 8-aminoquinoline directing group has been developed. This method proceeded through a migratory insertion/reductive-coupling process under mild conditions with a wide substrate scope and good functional group tolerance, providing direct access to the synthetically flexible 1,5-diynes. Moreover, the 1,2-dialkynylation products could be further converted to borate-ester- or azide-functionalized 1,5-dienes, ditriazole, β-diyne primary amide, and trisubstituted benzene.
已开发出一种前所未有的镍催化的、带有8-氨基喹啉导向基团的烯烃的还原1,2-二炔基化反应。该方法在温和条件下通过迁移插入/还原偶联过程进行，底物范围广，对官能团耐受性好，可直接合成具有合成灵活性的1,5-二炔。此外，1,2-二炔基化产物可进一步转化为硼酸酯或叠氮官能化的1,5-二烯、二唑、β-二炔伯酰胺和三取代苯。
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