Ronson Thomas O, Renders Evelien, Van Steijvoort Ben F, Wang Xubin, Wybon Clarence C D, Prokopcová Hana, Meerpoel Lieven, Maes Bert U W
Organic Synthesis, Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, 2020, Antwerp, Belgium.
Janssen Research & Development, Janssen Pharmaceutica NV, Turnhoutseweg 30, 2340, Beerse, Belgium.
Angew Chem Int Ed Engl. 2019 Jan 8;58(2):482-487. doi: 10.1002/anie.201810947. Epub 2018 Dec 11.
A new three-component reductive arylation of amides with stable reactants (iPrOH and arylboronate esters), making use of a 2-pyridinyl (Py) directing group, is described. The N-Py-amide substrates are readily prepared from carboxylic acids and PyNH , and the resulting N-Py-1-arylalkanamine reaction products are easily transformed into the corresponding chlorides by substitution of the HN-Py group with HCl. The 1-aryl-1-chloroalkane products allow substitution and cross-coupling reactions. Therefore, a general protocol for the transformation of carboxylic acids into a variety of functionalities is obtained. The Py-NH by-product can be recycled.
本文描述了一种利用2-吡啶基（Py）导向基团，使酰胺与稳定反应物（异丙醇和芳基硼酸酯）进行新型三组分还原芳基化反应的方法。N - Py - 酰胺底物可由羧酸和PyNH₂轻松制备，所得的N - Py - 1 - 芳基链烷胺反应产物可通过用HCl取代HN - Py基团而轻松转化为相应的氯化物。1 - 芳基 - 1 - 氯代烷产物可进行取代和交叉偶联反应。因此，获得了一种将羧酸转化为多种官能团的通用方法。Py - NH₂副产物可循环利用。
