Triazole-assisted ruthenium-catalyzed C-H arylation of aromatic amides

Hamad H. Al Mamari, Emelyne Diers, Lutz Ackermann*

*المؤلف المقابل لهذا العمل

نتاج البحث: المساهمة في مجلةArticleمراجعة النظراء

63 اقتباسات (Scopus)

ملخص

Site-selective ruthenium(II)-catalyzed direct arylation of amides was achieved through C-H cleavages with modular auxiliaries, derived from easily accessible 1,2,3-triazoles. The triazolyldimethylmethyl (TAM) bidentate directing group was prepared in a highly modular fashion through copper(I)-catalyzed 1,3-dipolar cycloaddition and allowed for ruthenium-catalyzed C-H arylations on arenes and heteroarenes, as well as alkenes, by using easy-to-handle aryl bromides as the arylating reagents. The triazole-assisted C-H activation strategy was found to be widely applicable, to occur under mild reaction conditions, and the catalytic system was tolerant of important electrophilic functionalities. Notably, the flexible triazole-based auxiliary proved to be a more potent directing group for the optimized ruthenium(II)-catalyzed direct arylations, compared with pyridyl-substituted amides or substrates derived from 8-aminoquinoline. Assisting activation: Ruthenium(II)-catalyzed C-H arylations of (hetero)arenes and alkenes have been achieved with aryl halides through removable bidentate auxiliaries derived from modular 1,2,3-triazoles (see scheme; TAM=triazolyldimethylmethyl).

اللغة الأصليةEnglish
الصفحات (من إلى)9739-9743
عدد الصفحات5
دوريةChemistry - A European Journal
مستوى الصوت20
رقم الإصدار31
المعرِّفات الرقمية للأشياء
حالة النشرPublished - يوليو 28 2014
منشور خارجيًانعم

ASJC Scopus subject areas

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