Triazole-Assisted Ruthenium-Catalyzed CH Arylation of Aromatic Amides
Site‐selective ruthenium(II)‐catalyzed direct arylation of amides was achieved through CH 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)‐cataly...
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Published in | Chemistry : a European journal Vol. 20; no. 31; pp. 9739 - 9743 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
Weinheim
WILEY-VCH Verlag
28.07.2014
WILEY‐VCH Verlag Wiley |
Subjects | |
Online Access | Get full text |
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Summary: | Site‐selective ruthenium(II)‐catalyzed direct arylation of amides was achieved through CH 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 CH arylations on arenes and heteroarenes, as well as alkenes, by using easy‐to‐handle aryl bromides as the arylating reagents. The triazole‐assisted CH 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 CH 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). |
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Bibliography: | ark:/67375/WNG-B2VL7GG4-M ArticleID:CHEM201403019 FP7 2007-2013 - No. 307535 istex:EC72666B6801C017A3D6ED287AD26D1814D8A558 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0947-6539 1521-3765 |
DOI: | 10.1002/chem.201403019 |