Efficient Heterogeneous Gold(I)-Catalyzed Direct C(sp2)–C(sp) Bond Functionalization of Arylalkynes through a Nitrogenation Process to Amides,Advanced Synthesis & Catalysis

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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

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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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