Pinxterhuis Erik B, Visser Paco, Esser Iwan, Gualtierotti Jean-Baptiste, Feringa Ben L
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands.
Angew Chem Int Ed Engl. 2018 Jul 20;57(30):9452-9455. doi: 10.1002/anie.201707760. Epub 2017 Oct 18.
The homocoupling of aryl halides and the heterocoupling of aryl halides with either aryl bromides or arenes bearing an ortho-lithiation directing group are presented. The use of a Pd catalyst, in combination with t-BuLi, allows for the rapid and efficient formation of a wide range of polyaromatic compounds in a one pot procedure bypassing the need for the separate preformation of an organometallic coupling partner. These polyaromatic structures are obtained in high yields, in 10 min at room temperature, with minimal waste generation (E-factors as low as 1.5) and without the need for strict inert conditions, making this process highly efficient and practical in comparison to classical methods. As illustration, several key intermediates of widely used BINOL-derived structures are readily prepared.
本文介绍了芳基卤化物的均偶联反应以及芳基卤化物与芳基溴化物或带有邻位锂化导向基团的芳烃的杂偶联反应。使用钯催化剂与叔丁基锂相结合，能够在一锅法中快速高效地形成多种多芳族化合物，无需单独预先制备有机金属偶联试剂。这些多芳族结构在室温下10分钟内即可高产率获得，产生的废物极少（E因子低至1.5），且无需严格的惰性条件，与传统方法相比，该过程高效且实用。作为示例，几种广泛使用的联萘酚衍生结构的关键中间体很容易制备出来。
