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Switching from 2-pyridination to difluoromethylation: ligand-enabled nickel-catalyzed reductive difluoromethylation of aryl iodides with difluoromethyl 2-pyridyl sulfone
Science China Chemistry ( IF 10.4 ) Pub Date : 2023-09-18 , DOI: 10.1007/s11426-023-1791-3
Wei Du , Qinyu Luo , Zhiqiang Wei , Xiu Wang , Chuanfa Ni , Jinbo Hu

The divergent reductive cross-coupling with an ambident electrophile is rare. Previously, we demonstrated a nickel-catalyzed reductive 2-pyridination of aryl iodides with difluoromethyl 2-pyridyl sulfone (2-PySO2CF2H) via selective C(sp2)–S bond cleavage of the sulfone by using a phosphine ligand. In this communication, we report a novel nickel-catalyzed reductive coupling of aryl iodides and 2-PySO2CF2H reagent, which constitutes a new method for aromatic difluoromethylation. The use of a tridentate terpyridine ligand is pivotal for the selective C(sp3)–S bond cleavage of the sulfone. This method employs readily available nickel catalyst and 2-PySO2CF2H as the difluoromethylation reagent, providing a facile access to difluoromethylarenes under mild reaction conditions without pre-generation of arylmetal reagents.



中文翻译:

从2-吡啶化转变为二氟甲基化:配体镍催化的芳基碘化物与二氟甲基2-吡啶基砜的还原二氟甲基化

与环境亲电子试剂的发散还原交叉偶联是罕见的。此前,我们通过使用膦配体选择性裂解砜的 C(sp 2 ) –S 键,演示了镍催化的芳基碘化物与二氟甲基 2-吡啶基砜 (2-PySO 2 CF 2 H )的还原 2-吡啶化反应。在本次通讯中,我们报道了一种新型的镍催化芳基碘化物与2-PySO 2 CF 2 H试剂的还原偶联,构成了芳香族二氟甲基化的新方法。三齿三联吡啶配体的使用对于砜的选择性 C(sp 3 )-S 键断裂至关重要。该方法采用现成的镍催化剂和 2-PySO2 CF 2 H作为二氟甲基化试剂,可以在温和的反应条件下轻松获得二氟甲基芳烃,而无需预先生成芳基金属试剂。

更新日期:2023-09-21
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