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Rh(III)-Catalyzed C(8)-H Activation of Quinoline N-Oxides: Regioselective C-Br and C-N Bond Formation.
J Org Chem. 2019 Oct 18; 84(20):12871-12880.JO

Abstract

A highly efficient and regioselective Rh(III)-catalyzed protocol for C8-bromination and amidation of quinoline N-oxide was developed. The transformation was found to be successful up to gram scale with excellent functional group tolerance and wide substrate scope. The mechanistic study revealed five-membered rhodacycle with quinoline N-oxide as a key intermediate for regioselective C8-functionalization. In addition, NFSI (N-fluorobis(phenylsulfonyl)-imide) was explored as an amidating reagent for C8-amidation of quinoline N-oxide for the first time.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Dhiman AK
Natural Product Chemistry and Process Development Division and AcSIR , CSIR-IHBT , Palampur 176061 , India.
Gupta SS
Natural Product Chemistry and Process Development Division and AcSIR , CSIR-IHBT , Palampur 176061 , India.
Sharma R
Natural Product Chemistry and Process Development Division and AcSIR , CSIR-IHBT , Palampur 176061 , India.
Kumar R
Natural Product Chemistry and Process Development Division and AcSIR , CSIR-IHBT , Palampur 176061 , India.
Sharma U
Natural Product Chemistry and Process Development Division and AcSIR , CSIR-IHBT , Palampur 176061 , India.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

31257883

Citation

Dhiman, Ankit Kumar, et al. "Rh(III)-Catalyzed C(8)-H Activation of Quinoline N-Oxides: Regioselective C-Br and C-N Bond Formation." The Journal of Organic Chemistry, vol. 84, no. 20, 2019, pp. 12871-12880.
Dhiman AK, Gupta SS, Sharma R, et al. Rh(III)-Catalyzed C(8)-H Activation of Quinoline N-Oxides: Regioselective C-Br and C-N Bond Formation. J Org Chem. 2019;84(20):12871-12880.
Dhiman, A. K., Gupta, S. S., Sharma, R., Kumar, R., & Sharma, U. (2019). Rh(III)-Catalyzed C(8)-H Activation of Quinoline N-Oxides: Regioselective C-Br and C-N Bond Formation. The Journal of Organic Chemistry, 84(20), 12871-12880. https://doi.org/10.1021/acs.joc.9b01538
Dhiman AK, et al. Rh(III)-Catalyzed C(8)-H Activation of Quinoline N-Oxides: Regioselective C-Br and C-N Bond Formation. J Org Chem. 2019 Oct 18;84(20):12871-12880. PubMed PMID: 31257883.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rh(III)-Catalyzed C(8)-H Activation of Quinoline N-Oxides: Regioselective C-Br and C-N Bond Formation. AU - Dhiman,Ankit Kumar, AU - Gupta,Shiv Shankar, AU - Sharma,Ritika, AU - Kumar,Rakesh, AU - Sharma,Upendra, Y1 - 2019/07/12/ PY - 2019/7/2/pubmed PY - 2019/7/2/medline PY - 2019/7/2/entrez SP - 12871 EP - 12880 JF - The Journal of organic chemistry JO - J Org Chem VL - 84 IS - 20 N2 - A highly efficient and regioselective Rh(III)-catalyzed protocol for C8-bromination and amidation of quinoline N-oxide was developed. The transformation was found to be successful up to gram scale with excellent functional group tolerance and wide substrate scope. The mechanistic study revealed five-membered rhodacycle with quinoline N-oxide as a key intermediate for regioselective C8-functionalization. In addition, NFSI (N-fluorobis(phenylsulfonyl)-imide) was explored as an amidating reagent for C8-amidation of quinoline N-oxide for the first time. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/31257883/Rh_III__Catalyzed_C_8__H_Activation_of_Quinoline_N_Oxides:_Regioselective_C_Br_and_C_N_Bond_Formation_ DB - PRIME DP - Unbound Medicine ER -