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Efficient Heterogeneous Gold(I)-Catalyzed Direct C(sp2)–C(sp) Bond Functionalization of Arylalkynes through a Nitrogenation Process to Amides
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2017-11-14 12:51:32 , DOI: 10.1002/adsc.201700783
Quan Nie 1 , Feiyan Yi 1 , Bin Huang 1 , Mingzhong Cai 1
Affiliation  

The first heterogeneous gold(I)-catalyzed direct C(sp2)–C(sp) bond functionalization of arylalkynes through a nitrogenation process to amides has been achieved by using an ordered mesoporous silica (MCM-41)-immobilized phosphine gold(I) complex [MCM-41-PPh3-AuCl] as catalyst and silver carbonate (Ag2CO3) as cocatalyst with trimethylsilyl azide (TMSN3) as a nitrogen source, yielding a variety of amides in moderate to excellent yields under mild conditions. This heterogeneous phosphine gold(I) complex shows the same turnover numbers as the homogeneous chloro(triphenylphosphine)gold(I) (Ph3PAuCl) and can easily be recovered by simple filtration of the reaction solution and recycled at least eight times without significant loss of activity, providing a novel, efficient, practical and economic method for the synthesis of amides from alkynes.

中文翻译:

高效异质金(I)催化的芳族炔烃通过氮酰胺化反应的直接C(sp2)–C(sp)键功能化

通过使用有序介孔二氧化硅(MCM-41)固定化的磷化膦金(I),实现了第一个非均相金(I)催化的芳族炔烃通过酰胺的氮化过程直接C(sp 2)–C(sp)键的官能化)络合物[MCM-41-PPh 3 -AuCl]作为催化剂,碳酸银(Ag 2 CO 3)作为助催化剂,叠氮化三甲基硅烷基酯(TMSN 3)作为氮源,在温和条件下可产生中等至优异收率的各种酰胺。这种异质的膦金(I)络合物显示出与均相的氯(三苯基膦)金(I)相同的营业额(Ph 3PAuCl)并可以通过简单过滤反应溶液而容易地回收,并循环至少八次而没有明显的活性损失,为从炔烃合成酰胺提供了一种新颖,有效,实用和经济的方法。
更新日期:2017-11-15
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