Halogen–Lithium Exchange of Sensitive (Hetero)aromatic Halides under Barbier Conditions in a Continuous Flow Set-Up,Synthesis

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Halogen–Lithium Exchange of Sensitive (Hetero)aromatic Halides under Barbier Conditions in a Continuous Flow Set-Up
Synthesis ( IF 2.2 ) Pub Date : 2020-09-02 , DOI: 10.1055/s-0040-1707259
Niels Weidmann ₁ , Rodolfo H. V. Nishimura ₂ , Paul Knochel ₁ , Johannes H. Harenberg ₁

Affiliation

In memory of Prof. Dr. Kilian Muñiz

Abstract

A halogen–lithium exchange reaction of (hetero)aromatic halides performed in the presence of various electrophiles such as aldehydes, ketones, Weinreb amides, and imines using BuLi as exchange reagent and a commercially available flow set-up is reported. The organolithiums generated in situ were instantaneously trapped with various electrophiles (Barbier conditions) resulting in the formation of polyfunctional (hetero)arenes. This method enables the functionalization of (hetero)arenes containing highly sensitive functional groups such as esters, which are not tolerated in batch conditions.

Publication History

Received: 21 July 2020

Accepted after revision: 29 July 2020

Publication Date:
02 September 2020 (online)

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

中文翻译：

Barbier条件下连续流动装置中敏感（杂）芳族卤化物的卤素-锂交换

纪念KilianMuñiz教授

抽象

据报道，在各种亲电试剂（例如醛，酮，Weinreb酰胺和亚胺）的存在下，使用BuLi作为交换试剂，进行了（杂）芳族卤化物的卤素-锂交换反应，并使用了市售的流动装置。用各种亲电试剂（Barbier条件）瞬时捕获原位生成的有机锂，从而形成多官能（杂）芳烃。这种方法能够使含有高度敏感的官能团（如酯）的（杂）芳烃官能化，而这些官能团在间歇条件下是不能容忍的。