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Microwave‐Promoted ortho‐C−H Bond (Hetero)arylation of Arylpyrimidines in Water Catalyzed by Ruthenium(II)−Carboxylate
ChemCatChem ( IF 4.5 ) Pub Date : 2018-07-16 , DOI: 10.1002/cctc.201800250
Miha Drev 1 , Uroš Grošelj 1 , Bine Ledinek 1, 2 , Franc Perdih 1 , Jurij Svete 1 , Bogdan Štefane 1 , Franc Požgan 1
Affiliation  

Efficient diarylation of ortho‐C−H bonds of 2‐arylpyrimidines was achieved by Ru(II)−carboxylate‐catalyzed reaction with aryl bromides in water, whereas meta‐substituted phenylpyrimidines selectively led to monoarylation. The reaction is strongly accelerated under microwave irradiation, and is compatible with various functional groups on both coupling partners. As established from Hammett plots, electron‐withdrawing groups on the pyrimidine substrates facilitate the arylation, while both, electron‐withdrawing and electron‐donating groups on the aryl bromides lead to a faster reaction. The C−H functionalization of 2‐arylpyrimidines with heteroaryl halides provides potential multidentate ligands.

中文翻译:

钌(II)-羧酸盐催化的水中芳基嘧啶的微波促进邻-C-H键(杂)芳基化

通过Ru(II)-羧酸盐与水中的芳基溴化物进行催化反应,可实现2-芳基嘧啶的邻位CH键的高效二芳基化,而间位取代的苯基嘧啶则选择性地导致单芳基化。在微波辐射下,该反应被强烈促进,并且与两个偶联配偶体上的各种官能团相容。根据Hammett图确定,嘧啶底物上的吸电子基团促进芳基化,而芳基溴化物上的吸电子基团和供电子基团则导致更快的反应。2-芳基嘧啶的CHH功能化与杂芳基卤化物可提供潜在的多齿配体。
更新日期:2018-07-16
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