Palladium-catalyzed C–N and C–O bond formation of N-substituted 4-bromo-7-azaindoles with amides, amines, amino acid esters and phenols

Rajendra Surasani, Dipak Kalita, A. V. Dhanunjaya Rao and K. B. Chandrasekhar
Beilstein J. Org. Chem. 2012, 8, 2004–2018. https://doi.org/10.3762/bjoc.8.227

Supporting Information

Supporting information, containing all experimental details and analytical data of all new compounds given in this article as well as their 1H, 13C NMR spectra and HRMS data, is provided.

Supporting Information File 1: Experimental procedures, analytical data and NMR spectra.
Format: PDF Size: 2.2 MB Download

Cite the Following Article

Palladium-catalyzed C–N and C–O bond formation of N-substituted 4-bromo-7-azaindoles with amides, amines, amino acid esters and phenols
Rajendra Surasani, Dipak Kalita, A. V. Dhanunjaya Rao and K. B. Chandrasekhar
Beilstein J. Org. Chem. 2012, 8, 2004–2018. https://doi.org/10.3762/bjoc.8.227

How to Cite

Surasani, R.; Kalita, D.; Rao, A. V. D.; Chandrasekhar, K. B. Beilstein J. Org. Chem. 2012, 8, 2004–2018. doi:10.3762/bjoc.8.227

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Umehara, A.; Shimizu, S.; Sasaki, M. Synthesis of Bulky N‐Acyl Heterocycles by DMAPO/Boc2O‐Mediated One‐Pot Direct N‐Acylation of Less Nucleophilic N‐Heterocycles with α‐Fully Substituted Carboxylic Acids. Advanced Synthesis & Catalysis 2023, 365, 2367–2376. doi:10.1002/adsc.202300487
  • Dhara, S.; Saha, M.; Das, A. R. Ligand-free access to benzisothiazolones and benzisoselenazolones through NiFe2O4 catalyzed concomitant annulation of 2-halobenzanilides with chalcogens and their late-stage transformations. New Journal of Chemistry 2022, 46, 19501–19513. doi:10.1039/d2nj04326b
  • Song, G.; Yang, L.; Li, J.-S.; Tang, W.; Zhang, W.; Cao, R.; Wang, C.; Xiao, J.; Xue, D. Chiral Arylated Amines via C-N Coupling of Chiral Amines with Aryl Bromides Promoted by Light. Angewandte Chemie (International ed. in English) 2021, 60, 21536–21542. doi:10.1002/anie.202108587
  • Song, G.; Yang, L.; Li, J.; Tang, W.; Zhang, W.; Cao, R.; Wang, C.; Xiao, J.; Xue, D. Chiral Arylated Amines via C−N Coupling of Chiral Amines with Aryl Bromides Promoted by Light. Angewandte Chemie 2021, 133, 21706–21712. doi:10.1002/ange.202108587
  • Das, T.; Ranjan, A.; Sieroń, L.; Maniukiewicz, W.; Das, S. Direct Synthesis, Characterization and Theoretical Studies of N-(6-Amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)benzamide Derivatives. ChemistrySelect 2021, 6, 726–732. doi:10.1002/slct.202004745
  • Murinov, Y. I.; Golubyatnikova, L. G.; Khisamutdinov, R. A.; Badamshin, A. G.; Dokichev, V. A. Palladium-Promoted Carbon–Nitrogen Bond Cleavage in 1,3,5-Triazinane Derivatives. Russian Journal of General Chemistry 2020, 90, 2048–2052. doi:10.1134/s1070363220110055
  • Kannaboina, P.; Mondal, K.; Laha, J. K.; Das, P. Recent advances in the global ring functionalization of 7-azaindoles. Chemical communications (Cambridge, England) 2020, 56, 11749–11762. doi:10.1039/d0cc04264a
  • Liu, S.; Heng, Y.; Jiao, L.-Y.; Zhang, J.-H.; Zhao, C.; Ma, Y.; Yang, X. Regioselective deoxygenative chalcogenation of 7-azindole N-oxides promoted by I2/PEG-200. Organic & biomolecular chemistry 2019, 17, 10073–10087. doi:10.1039/c9ob02044f
  • Kawamata, Y.; Vantourout, J. C.; Hickey, D. P.; Bai, P.; Chen, L.; Hou, Q.; Qiao, W.; Barman, K.; Edwards, M. A.; Garrido-Castro, A. F.; deGruyter, J. N.; Nakamura, H.; Knouse, K. W.; Qin, C.; Clay, K. J.; Bao, D.; Li, C.; Starr, J. T.; Garcia-Irizarry, C. N.; Sach, N. W.; White, H. S.; Neurock, M.; Minteer, S. D.; Baran, P. S. Electrochemically Driven, Ni-Catalyzed Aryl Amination: Scope, Mechanism, and Applications. Journal of the American Chemical Society 2019, 141, 6392–6402. doi:10.1021/jacs.9b01886
  • Hobson, C.; Perryman, M. S.; Kirby, G.; Clarkson, G. J.; Fox, D. J. Synthesis of enantiomerically-enriched N-aryl amino-amides via a Jocic-type reaction. Tetrahedron Letters 2018, 59, 3965–3968. doi:10.1016/j.tetlet.2018.09.046
  • Dhineshkumar, J.; Gadde, K.; Prabhu, K. R. Substituent-Directed Regioselective Azidation: Copper-Catalyzed C–H Azidation and Iodine-Catalyzed Dearomatizative Azidation of Indole. The Journal of organic chemistry 2017, 83, 228–235. doi:10.1021/acs.joc.7b02591
  • Pajtás, D.; Kónya, K.; Kiss-Szikszai, A.; Džubák, P.; Pethő, Z.; Varga, Z.; Panyi, G.; Patonay, T. Optimization of the Synthesis of Flavone-Amino Acid and Flavone-Dipeptide Hybrids via Buchwald-Hartwig Reaction. The Journal of organic chemistry 2017, 82, 4578–4587. doi:10.1021/acs.joc.7b00124
  • Moss, S. G.; Pocock, I. A.; Sweeney, J. B. Tandem Aryne-Capture/Sigmatropic Rearrangement as a Metal-Free Entry to Functionalized N-Aryl Pyrrolidines. Chemistry (Weinheim an der Bergstrasse, Germany) 2016, 23, 101–104. doi:10.1002/chem.201605290
  • Krishnan, K. K.; Ujwaldev, S. M.; Sindhu, K. S.; Anilkumar, G. Recent advances in the transition metal catalyzed etherification reactions. Tetrahedron 2016, 72, 7393–7407. doi:10.1016/j.tet.2016.10.002
  • Sharif, S.; Mitchell, D.; Rodriguez, M. J.; Farmer, J. L.; Organ, M. G. N-Heteroarylation of Optically Pure α-Amino Esters using the Pd-PEPPSI-IPentCl -o-picoline Pre-Catalyst. Chemistry (Weinheim an der Bergstrasse, Germany) 2016, 22, 14860–14863. doi:10.1002/chem.201603933
  • King, S. M.; Buchwald, S. L. Development of a Method for the N-Arylation of Amino Acid Esters with Aryl Triflates. Organic letters 2016, 18, 4128–4131. doi:10.1021/acs.orglett.6b02082
  • Han, S.; Doi, R.; Stoltz, B. M. Nickel‐Catalyzed Intramolecular C−O Bond Formation: Synthesis of Cyclic Enol Ethers. Angewandte Chemie 2016, 128, 7563–7566. doi:10.1002/ange.201601991
  • Han, S.-J.; Doi, R.; Stoltz, B. M. Nickel-Catalyzed Intramolecular C-O Bond Formation: Synthesis of Cyclic Enol Ethers. Angewandte Chemie (International ed. in English) 2016, 55, 7437–7440. doi:10.1002/anie.201601991
  • Hareesh, H.; Minchitha, K.; Nagaraju, N.; Kathyayini, N. Catalytic role of Cu(I) species in Cu2O/CuI supported on MWCNTs in the oxidative amidation of aryl aldehydes with 2-aminopyridines. Chinese Journal of Catalysis 2015, 36, 1825–1836. doi:10.1016/s1872-2067(15)60964-0
  • Plas, A.; Martin, C.; Joubert, N.; Viaud-Massuard, M.-C. Palladium-Catalyzed Amination of N-Free 2-Chloro-7-azaindole. Organic letters 2015, 17, 4710–4713. doi:10.1021/acs.orglett.5b02173
Other Beilstein-Institut Open Science Activities