Tags

Type your tag names separated by a space and hit enter

Palladium-catalyzed regioselective C-5 arylation of protected L-histidine: microwave-assisted C-H activation adjacent to donor arm.
J Org Chem. 2013 Nov 01; 78(21):10954-9.JO

Abstract

An efficient, microwave-assisted direct C-H arylation at the C-5 position of fully protected L-histidine has been achieved via a palladium-catalyzed transformation reaction. This highly regioselective reaction has been applied to synthesize a series of protected 5-aryl-L-histidines using aryl iodides as coupling partners, in good to excellent yields. The reaction is compatible with substrates possessing electron-donating or electron-withdrawing substituents and offers high reactive functional group tolerance.

Links

Publisher Full Text (DOI)

Authors+Show Affiliations

Mahindra A
Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research , Sector 67, SAS Nagar, Punjab 160 062, India.
Bagra N
No affiliation info available
Jain R
No affiliation info available

MeSH

CatalysisElectronsHistidineHydrogen BondingIodidesMicrowavesMolecular StructurePalladiumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

24098973

Citation

Mahindra, Amit, et al. "Palladium-catalyzed Regioselective C-5 Arylation of Protected L-histidine: Microwave-assisted C-H Activation Adjacent to Donor Arm." The Journal of Organic Chemistry, vol. 78, no. 21, 2013, pp. 10954-9.
Mahindra A, Bagra N, Jain R. Palladium-catalyzed regioselective C-5 arylation of protected L-histidine: microwave-assisted C-H activation adjacent to donor arm. J Org Chem. 2013;78(21):10954-9.
Mahindra, A., Bagra, N., & Jain, R. (2013). Palladium-catalyzed regioselective C-5 arylation of protected L-histidine: microwave-assisted C-H activation adjacent to donor arm. The Journal of Organic Chemistry, 78(21), 10954-9. https://doi.org/10.1021/jo401934q
Mahindra A, Bagra N, Jain R. Palladium-catalyzed Regioselective C-5 Arylation of Protected L-histidine: Microwave-assisted C-H Activation Adjacent to Donor Arm. J Org Chem. 2013 Nov 1;78(21):10954-9. PubMed PMID: 24098973.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium-catalyzed regioselective C-5 arylation of protected L-histidine: microwave-assisted C-H activation adjacent to donor arm. AU - Mahindra,Amit, AU - Bagra,Nitin, AU - Jain,Rahul, Y1 - 2013/10/18/ PY - 2013/10/9/entrez PY - 2013/10/9/pubmed PY - 2014/6/12/medline SP - 10954 EP - 9 JF - The Journal of organic chemistry JO - J Org Chem VL - 78 IS - 21 N2 - An efficient, microwave-assisted direct C-H arylation at the C-5 position of fully protected L-histidine has been achieved via a palladium-catalyzed transformation reaction. This highly regioselective reaction has been applied to synthesize a series of protected 5-aryl-L-histidines using aryl iodides as coupling partners, in good to excellent yields. The reaction is compatible with substrates possessing electron-donating or electron-withdrawing substituents and offers high reactive functional group tolerance. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/24098973/Palladium_catalyzed_regioselective_C_5_arylation_of_protected_L_histidine:_microwave_assisted_C_H_activation_adjacent_to_donor_arm_ L2 - https://doi.org/10.1021/jo401934q DB - PRIME DP - Unbound Medicine ER -