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Amidines for versatile ruthenium(II)-catalyzed oxidative C-H activations with internal alkynes and acrylates.
Chemistry. 2014 Apr 25; 20(18):5403-8.C

Abstract

Cationic ruthenium complexes derived from KPF6 or AgOAc enabled efficient oxidative CH functionalizations on aryl and heteroaryl amidines. Thus, oxidative annulations of diversely decorated internal alkynes provided expedient access to 1-aminoisoquinolines, while catalyzed C-H activations with substituted acrylates gave rise to structurally novel 1-iminoisoindolines. The powerful ruthenium(II) catalysts displayed a remarkably high site-, regio- and, chemoselectivity. Therefore, the catalytic system proved tolerant of a variety of important electrophilic functional groups. Detailed mechanistic studies provided strong support for the cationic ruthenium(II) catalysts to operate by a facile, reversible C-H activation.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Li J
Institut für Organische und Biomolekulare Chemie, Georg-August-Universität, Tammannstrasse 2, 37077 Göttingen (Germany), Fax: (+49) 551-39-6777.
John M
No affiliation info available
Ackermann L
No affiliation info available

MeSH

AcrylatesAlkynesAmidinesCatalysisCationsIsoquinolinesOxidation-ReductionRuthenium

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

24677682

Citation

Li, Jie, et al. "Amidines for Versatile ruthenium(II)-catalyzed Oxidative C-H Activations With Internal Alkynes and Acrylates." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 20, no. 18, 2014, pp. 5403-8.
Li J, John M, Ackermann L. Amidines for versatile ruthenium(II)-catalyzed oxidative C-H activations with internal alkynes and acrylates. Chemistry. 2014;20(18):5403-8.
Li, J., John, M., & Ackermann, L. (2014). Amidines for versatile ruthenium(II)-catalyzed oxidative C-H activations with internal alkynes and acrylates. Chemistry (Weinheim an Der Bergstrasse, Germany), 20(18), 5403-8. https://doi.org/10.1002/chem.201304944
Li J, John M, Ackermann L. Amidines for Versatile ruthenium(II)-catalyzed Oxidative C-H Activations With Internal Alkynes and Acrylates. Chemistry. 2014 Apr 25;20(18):5403-8. PubMed PMID: 24677682.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Amidines for versatile ruthenium(II)-catalyzed oxidative C-H activations with internal alkynes and acrylates. AU - Li,Jie, AU - John,Michael, AU - Ackermann,Lutz, Y1 - 2014/03/27/ PY - 2013/12/18/received PY - 2014/3/29/entrez PY - 2014/3/29/pubmed PY - 2015/4/23/medline KW - CH activation KW - alkenylation KW - alkynes KW - annulation KW - reaction mechanisms KW - ruthenium SP - 5403 EP - 8 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 20 IS - 18 N2 - Cationic ruthenium complexes derived from KPF6 or AgOAc enabled efficient oxidative CH functionalizations on aryl and heteroaryl amidines. Thus, oxidative annulations of diversely decorated internal alkynes provided expedient access to 1-aminoisoquinolines, while catalyzed C-H activations with substituted acrylates gave rise to structurally novel 1-iminoisoindolines. The powerful ruthenium(II) catalysts displayed a remarkably high site-, regio- and, chemoselectivity. Therefore, the catalytic system proved tolerant of a variety of important electrophilic functional groups. Detailed mechanistic studies provided strong support for the cationic ruthenium(II) catalysts to operate by a facile, reversible C-H activation. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/24677682/Amidines_for_versatile_ruthenium_II__catalyzed_oxidative_C_H_activations_with_internal_alkynes_and_acrylates_ DB - PRIME DP - Unbound Medicine ER -