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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.

DOI:10.1002/open.202400180
PMID:39051713
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12056928/
Abstract

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.

摘要

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。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2394/12056928/ecd4ea35261f/OPEN-13-e202400180-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2394/12056928/f3350b3422f6/OPEN-13-e202400180-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2394/12056928/e4ea241811d5/OPEN-13-e202400180-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2394/12056928/3f4b2b2cdc81/OPEN-13-e202400180-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2394/12056928/0197c2dc26a0/OPEN-13-e202400180-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2394/12056928/307f111dac23/OPEN-13-e202400180-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2394/12056928/92d1830b83d0/OPEN-13-e202400180-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2394/12056928/2e8e2346efcd/OPEN-13-e202400180-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2394/12056928/ecd4ea35261f/OPEN-13-e202400180-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2394/12056928/f3350b3422f6/OPEN-13-e202400180-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2394/12056928/e4ea241811d5/OPEN-13-e202400180-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2394/12056928/3f4b2b2cdc81/OPEN-13-e202400180-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2394/12056928/0197c2dc26a0/OPEN-13-e202400180-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2394/12056928/307f111dac23/OPEN-13-e202400180-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2394/12056928/92d1830b83d0/OPEN-13-e202400180-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2394/12056928/2e8e2346efcd/OPEN-13-e202400180-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2394/12056928/ecd4ea35261f/OPEN-13-e202400180-g004.jpg

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C-H Activation: Toward Sustainability and Applications.
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