咪唑并[2,1-b]噻唑直接C-H芳基化反应中过渡金属驱动的选择性
Transition Metal-Driven Selectivity in Direct C-H Arylation of Imidazo[2,1-b]Thiazole.
作者信息
Del Vecchio Antonio, Rosadoni Elisabetta, Ballerini Lorenzo, Cuzzola Angela, Lipparini Filippo, Ronchi Paolo, Guariento Sara, Biagetti Matteo, Lessi Marco, Bellina Fabio
机构信息
Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Via Giuseppe Moruzzi, 13, 56124, Pisa, Italy.
Chemistry Research and Drug Design, Chiesi Farmaceutici S.p.A, 43122, Parma, Italy.
出版信息
ChemistryOpen. 2024 Nov;13(11):e202400180. doi: 10.1002/open.202400180. Epub 2024 Jul 25.
A selective direct arylation of the different Csp2-H bonds of imidazo[2,1-b]thiazole with (hetero) aryl halides can be achieved simply by switching from a palladium catalyst system to the use of stoichiometric amounts of copper. The observed selectivity, also rationalized by DFT calculations, can be explained by a change in the mechanistic pathways between electrophilic palladation and base-promoted C-H metalation.
通过从钯催化剂体系转换为使用化学计量的铜，可实现咪唑并[2,1 - b]噻唑不同Csp2 - H键与（杂）芳基卤化物的选择性直接芳基化。通过DFT计算也得到合理解释的观察到的选择性，可以通过亲电钯化和碱促进的C - H金属化之间机理途径的变化来解释。
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