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Cobalt(iii) catalyzed C-8 selective C-H and C-O coupling of quinoline N-oxide with internal alkynes via C-H activation and oxygen atom transfer.
Chem Commun (Camb). 2016 Jan 25; 52(7):1338-41.CC

Abstract

An efficient, scalable, atom-economical, regio-selective air stable Cp*Co(iii) catalyzed C-H and C-O coupling via a C-H activation/oxygen atom transfer reaction of quinoline N-oxide and an internal alkyne is reported. Such a catalytic transformation is witnessed for the first time with a cobalt catalyst and using N-oxide as a traceless directing group, in contrast to the existing literature. The developed synthetic methodology is straightforward and possesses various functional group tolerances, including heterocycles.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Barsu N
Fine Chemical Laboratory, Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, UP, India. basker@iitk.ac.in.
Sen M
Fine Chemical Laboratory, Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, UP, India. basker@iitk.ac.in.
Premkumar JR
Center for Molecular Modelling, Indian Institute of Chemical Technology, Hyderabad - 500 067, India.
Sundararaju B
Fine Chemical Laboratory, Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, UP, India. basker@iitk.ac.in.

MeSH

AlkynesCatalysisCobaltQuinolines

Pub Type(s)

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

Language

eng

PubMed ID

26695530

Citation

Barsu, Nagaraju, et al. "Cobalt(iii) Catalyzed C-8 Selective C-H and C-O Coupling of Quinoline N-oxide With Internal Alkynes Via C-H Activation and Oxygen Atom Transfer." Chemical Communications (Cambridge, England), vol. 52, no. 7, 2016, pp. 1338-41.
Barsu N, Sen M, Premkumar JR, et al. Cobalt(iii) catalyzed C-8 selective C-H and C-O coupling of quinoline N-oxide with internal alkynes via C-H activation and oxygen atom transfer. Chem Commun (Camb). 2016;52(7):1338-41.
Barsu, N., Sen, M., Premkumar, J. R., & Sundararaju, B. (2016). Cobalt(iii) catalyzed C-8 selective C-H and C-O coupling of quinoline N-oxide with internal alkynes via C-H activation and oxygen atom transfer. Chemical Communications (Cambridge, England), 52(7), 1338-41. https://doi.org/10.1039/c5cc08736h
Barsu N, et al. Cobalt(iii) Catalyzed C-8 Selective C-H and C-O Coupling of Quinoline N-oxide With Internal Alkynes Via C-H Activation and Oxygen Atom Transfer. Chem Commun (Camb). 2016 Jan 25;52(7):1338-41. PubMed PMID: 26695530.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Cobalt(iii) catalyzed C-8 selective C-H and C-O coupling of quinoline N-oxide with internal alkynes via C-H activation and oxygen atom transfer. AU - Barsu,Nagaraju, AU - Sen,Malay, AU - Premkumar,J Richard, AU - Sundararaju,Basker, PY - 2015/12/24/entrez PY - 2015/12/24/pubmed PY - 2016/10/11/medline SP - 1338 EP - 41 JF - Chemical communications (Cambridge, England) JO - Chem Commun (Camb) VL - 52 IS - 7 N2 - An efficient, scalable, atom-economical, regio-selective air stable Cp*Co(iii) catalyzed C-H and C-O coupling via a C-H activation/oxygen atom transfer reaction of quinoline N-oxide and an internal alkyne is reported. Such a catalytic transformation is witnessed for the first time with a cobalt catalyst and using N-oxide as a traceless directing group, in contrast to the existing literature. The developed synthetic methodology is straightforward and possesses various functional group tolerances, including heterocycles. SN - 1364-548X UR - https://www.unboundmedicine.com/medline/citation/26695530/Cobalt_iii__catalyzed_C_8_selective_C_H_and_C_O_coupling_of_quinoline_N_oxide_with_internal_alkynes_via_C_H_activation_and_oxygen_atom_transfer_ DB - PRIME DP - Unbound Medicine ER -