Synthesis ( IF 2.2 ) Pub Date : 2018-03-08 , DOI: 10.1055/s-0036-1591953 William Erb 1 , Florence Mongin 1 , Nahida Brikci-Nigassa 1, 2 , Ghenia Bentabed-Ababsa 2
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Published as part of the Special Section on the Main Group Metal Chemistry Symposium
Abstract
Deprotometalation is an efficient method to functionalize regioselectively aromatic compounds including heterocycles. This short review shows how it is possible to intercept aryllithiums (and other polar arylmetals) as soon as they are formed by in situ ‘trans-metal trapping’. The approach avoids long contact between aryllithiums and sensitive substrates. In addition, it allows less activated substrates to be deprotonated by non-nucleophilic lithium amides. While using chlorosilanes and borates still arouses the interest of chemists, more recently, methods based on zinc, aluminum and gallium have appeared, enabling this chemistry to grow dramatically.
1 Introduction
2 Silicon-Based In Situ Traps
3 Boron-Based In Situ Traps
4 Zinc-Based In Situ Traps
5 Aluminum- and Gallium-Based In Situ Traps
6 Other In Situ Traps
7 Continuous-Flow In Situ ‘Trans-Metal Trapping’
8 Conclusion
Deprotometalation is an efficient method to functionalize regioselectively aromatic compounds including heterocycles. This short review shows how it is possible to intercept aryllithiums (and other polar arylmetals) as soon as they are formed by in situ ‘trans-metal trapping’. The approach avoids long contact between aryllithiums and sensitive substrates. In addition, it allows less activated substrates to be deprotonated by non-nucleophilic lithium amides. While using chlorosilanes and borates still arouses the interest of chemists, more recently, methods based on zinc, aluminum and gallium have appeared, enabling this chemistry to grow dramatically.
1 Introduction
2 Silicon-Based In Situ Traps
3 Boron-Based In Situ Traps
4 Zinc-Based In Situ Traps
5 Aluminum- and Gallium-Based In Situ Traps
6 Other In Situ Traps
7 Continuous-Flow In Situ ‘Trans-Metal Trapping’
8 Conclusion
中文翻译：
原位“跨金属陷印”：一种有效的方法来扩展芳族金属去金属化的范围
作为主体金属化学专题讨论会特别部分的一部分出版
抽象的
去原金属化是使包括杂环的区域选择性芳族化合物官能化的有效方法。这篇简短的评论展示了通过原位“跨金属捕获”形成芳基锂（以及其他极性芳基金属）后，它们如何能够被拦截。该方法避免了芳基锂和敏感衬底之间的长时间接触。另外，它允许较少活化的底物被非亲核性锂酰胺去质子化。尽管使用氯硅烷和硼酸盐仍然引起了化学家的兴趣，但近来出现了基于锌，铝和镓的方法，使这种化学方法得以迅速发展。
1引言
2个基于硅的原位陷阱
3种基于硼的原位陷阱
4个基于锌的原位陷阱
5个基于铝和镓的原位陷阱
6个其他原位陷阱
7连续流原位“跨金属陷印”
8结论
去原金属化是使包括杂环的区域选择性芳族化合物官能化的有效方法。这篇简短的评论展示了通过原位“跨金属捕获”形成芳基锂（以及其他极性芳基金属）后，它们如何能够被拦截。该方法避免了芳基锂和敏感衬底之间的长时间接触。另外，它允许较少活化的底物被非亲核性锂酰胺去质子化。尽管使用氯硅烷和硼酸盐仍然引起了化学家的兴趣，但近来出现了基于锌，铝和镓的方法，使这种化学方法得以迅速发展。
1引言
2个基于硅的原位陷阱
3种基于硼的原位陷阱
4个基于锌的原位陷阱
5个基于铝和镓的原位陷阱
6个其他原位陷阱
7连续流原位“跨金属陷印”
8结论
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