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α-MsO/TsO/Cl ketones as oxidized alkyne equivalents: redox-neutral rhodium(III)-catalyzed C-H activation for the synthesis of N-heterocycles.
Angew Chem Int Ed Engl. 2014 Mar 03; 53(10):2754-8.AC

Abstract

α-Halo and pseudohalo ketones are used for the first time as C(sp(3))-based electrophiles in transition-metal-catalyzed C-H activation and as oxidized alkyne equivalents in Rh(III)-catalyzed redox-neutral annulations to generate diverse N-heterocycles. This transformation is efficient and scalable. Due to the mild reaction conditions, a variety of functional groups could be tolerated.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Yu DG
Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstrasse 40, 48149 Münster (Germany) http://www.uni-muenster.de/Chemie.oc/glorius/
de Azambuja F
No affiliation info available
Glorius F
No affiliation info available

MeSH

AlkynesBenzenesulfonatesCatalysisChloridesHeterocyclic CompoundsMesylatesMolecular StructureOxidation-ReductionRhodium

Pub Type(s)

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

Language

eng

PubMed ID

24488682

Citation

Yu, Da-Gang, et al. "Α-MsO/TsO/Cl Ketones as Oxidized Alkyne Equivalents: Redox-neutral rhodium(III)-catalyzed C-H Activation for the Synthesis of N-heterocycles." Angewandte Chemie (International Ed. in English), vol. 53, no. 10, 2014, pp. 2754-8.
Yu DG, de Azambuja F, Glorius F. Α-MsO/TsO/Cl ketones as oxidized alkyne equivalents: redox-neutral rhodium(III)-catalyzed C-H activation for the synthesis of N-heterocycles. Angew Chem Int Ed Engl. 2014;53(10):2754-8.
Yu, D. G., de Azambuja, F., & Glorius, F. (2014). Α-MsO/TsO/Cl ketones as oxidized alkyne equivalents: redox-neutral rhodium(III)-catalyzed C-H activation for the synthesis of N-heterocycles. Angewandte Chemie (International Ed. in English), 53(10), 2754-8. https://doi.org/10.1002/anie.201310272
Yu DG, de Azambuja F, Glorius F. Α-MsO/TsO/Cl Ketones as Oxidized Alkyne Equivalents: Redox-neutral rhodium(III)-catalyzed C-H Activation for the Synthesis of N-heterocycles. Angew Chem Int Ed Engl. 2014 Mar 3;53(10):2754-8. PubMed PMID: 24488682.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - α-MsO/TsO/Cl ketones as oxidized alkyne equivalents: redox-neutral rhodium(III)-catalyzed C-H activation for the synthesis of N-heterocycles. AU - Yu,Da-Gang, AU - de Azambuja,Francisco, AU - Glorius,Frank, Y1 - 2014/02/02/ PY - 2013/11/26/received PY - 2014/2/4/entrez PY - 2014/2/4/pubmed PY - 2014/10/23/medline KW - CH activation KW - N-heterocycles KW - isoquinolones KW - ketones KW - rhodium catalysis SP - 2754 EP - 8 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 53 IS - 10 N2 - α-Halo and pseudohalo ketones are used for the first time as C(sp(3))-based electrophiles in transition-metal-catalyzed C-H activation and as oxidized alkyne equivalents in Rh(III)-catalyzed redox-neutral annulations to generate diverse N-heterocycles. This transformation is efficient and scalable. Due to the mild reaction conditions, a variety of functional groups could be tolerated. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/24488682/��_MsO/TsO/Cl_ketones_as_oxidized_alkyne_equivalents:_redox_neutral_rhodium_III__catalyzed_C_H_activation_for_the_synthesis_of_N_heterocycles_ DB - PRIME DP - Unbound Medicine ER -