Nashrieh Shimi va Mohandesi Shimi Iran

Nashrieh Shimi va Mohandesi Shimi Iran

Synthesis of N-Aryl Amine Derivatives Using Copper Salts Catalysts

Document Type : Research Article

Authors
Magid Ghazanfarpour Darjani
Mahboobeh Babapour-Kooshalshahi
Leila Mohamad-Alikhani
Young Research and Elite Club, Islamic Azad University, Buinzahra Branch, Buinzahra, I.R. IRAN
Abstract
Unsymmetrical piperazines are key constituents of many anti-psychotic pharmaceuticals and bioactive compounds. Given that the selective introduction of an aryl and alkyl motif onto the piperazine skeleton is not always straightforward, direct arylation or alkylation of 1,4-diaza-bicyclo[2.2.2]octane would obviate the inefficiencies associated with the preparation of these target valuable molecules. We have utilized alkyl chlorides as the alkyl source, aryl triflates as the active aryl source, and 1,4-diaza-bicyclo[2.2.2]octane for the synthesis of N-alkyl-N′-arylpiperazines. The optimum conditions are developed using CuCl and t-BuOLi in PEG-400. Substrates bearing electron-deficient as well as electron-rich groups were successfully coupled under the optimum reaction conditions.  
Keywords
Aryl triflate
Unsymmetrical pipirazine
Cross-coupling reaction
Bulky base
Copper Chloride
Polyethylene glycol-400

Subjects

[1] خانلری، طیبه؛ تهیه پلیمر حمایت کننده پالادیوم، برپایه پلی­وینیل الکل و استفاده از آن در واکنش هک، نشریهشیمیومهندسیشیمیایران، (2)34: 25 تا 40 (1394).
[2] امینی، مجتبی؛ بهرامی حیدرلو، دینا؛ باقرزاده، مجتبی؛ نانوذره­های پالادیم تثبیت شده بر روی بستر روی اکسید به­عنوان کاتالیستی مؤثر در واکنش جفت شدن هک، نشریهشیمیومهندسیشیمیایران، (2)35: 21تا 29 (1395).
[3] Marset X., Khoshnood A., Sotorríos L., Gómez-Bengoa E., Alonso D. A., Ramón D. J., Deep Eutectic Solvent Compatible Metallic Catalysts: Cationic Pyridiniophosphine Ligands in Palladium Catalyzed Cross‐Coupling Reactions,Chem. Cat. Chem., 9: 1269-1275 (2017).
[4] Sandfort F., O'Neill M.J., Cornella J., Wimmer L., Baran P.S., Alkyl−(Hetero)Aryl Bond Formation via Decarboxylative Cross-Coupling: A Systematic Analysis,Angew. Chem. Int. Ed., 56: 3319-3323 (2017).
[5] Brambilla M., Tredwell M., Palladium-Catalyzed Suzuki–Miyaura Cross-Coupling of Secondary α-(Trifluoromethyl)benzyl Tosylates,Angew. Chem. Int. Ed., 56: 11981-11985 (2017).
[6] Serra J., Parella T., Ribas X., Au(III)-aryl Intermediates in Oxidant-Free C–N and C–O Cross-Coupling Catalysis, Chem. Sci., 8: 946-952 (2017).
[7] Guram A.S., Buchwald S.L., Palladium-Catalyzed Aromatic Aminations with in situ Generated Aminostannanes,J. Am. Chem. Soc., 116: 7901-7902 (1994).
[8] Clark J.S.K., Voth C.N., Ferguson M.J., Stradiotto M., Evaluating 1,1′-Bis(phosphino)ferrocene Ancillary Ligand Variants in the Nickel-Catalyzed C–N Cross-Coupling of (Hetero)aryl Chlorides, Organometallics., 36: 679-686 (2017).
[9] Khalaj M., Ghazanfarpour-Darjani M., Cross-Coupling Reaction of Aryl Diazonium Salts with Azodicarboxylate Using FeCl2, RSC Adv., 5: 80698-80701 (2015).
[10] Yavari I., Ghazanfarpour-Darjani M., Bayat M.J., Malekafzali A., Sodium Hydride Induced N-Arylation of Diisopropyl Azodicarboxylate by Aryl Trifluoromethanesulfonates, Synlett., 26: 942-944 (2015).
[11] Chan K.S.L., Wasa M., Chu L., Laforteza B.N., Miura M., Yu J.Q., Ligand-Enabled Cross-Coupling of C(sp3)–H Bonds with Arylboron Reagents via Pd(II)/Pd(0) Catalysis, Nature Chemistry., 6: 146-150 (2014).
[12] De S., YinJ., Ma D., Copper-Catalyzed Coupling Reaction of (Hetero)Aryl Chlorides and Amides, Org. Lett., 19: 4864–4867 (2017).
[13] Ma D., Cai Q., Copper/Amino Acid Catalyzed Cross-Couplings of Aryl and Vinyl Halides with Nucleophiles, Acc. Chem. Res., 41: 1450–1460 (2008).
[14] DaiJ.L., ShaoN.Q., ZhangJ., JiaR.P., Wang D.H., Cu(II)-Catalyzed ortho-Selective Aminomethylation of Phenols, J. Am. Chem. Soc., 139: 12390–12393 (2017).
[15] Gao J., BhuniaS., WangK., GanL., Xia S., Ma D., Discovery of N-(Naphthalen-1-yl)-N′-alkyl Oxalamide Ligands Enables Cu-Catalyzed Aryl Amination with High Turnovers, Org. Lett., 19: 2809–2812 (2017).
[16] Taylor R.D., MacCoss M., Lawson A.D.G., Rings in Drugs, J. Med. Chem., 57: 5845-5859 (2014).
[17] Zhang T.Y., The Evolving Landscape of Heterocycles in Drugs and Drug Candidates,Adv. Heterocycl. Chem., 121: 1-12 (2017).
[18] Vitaku E., Smith D.T., Njardarson J.T., Analysis of the Structural Diversity, Substitution Patterns, and Frequency of Nitrogen Heterocycles among U.S. FDA Approved Pharmaceuticals,J. Med. Chem., 57: 10257-10274 (2014).
[19] Gettys K.E., Ye Z., Dai M., Recent Advances in Piperazine Synthesis, Synthesis,49: 2589–2604 (2017).
[20] Maras N., Polanc S., Kocevar M.,Ring-Opening Reactions of 1,4-diazabicyclo[2.2.2]octane (DABCO) Derived Quaternary Ammonium Salts with Phenols and Related Nucleophiles, Org. Biomol. Chem., 10: 1300-1310 (2012).
[21] Zhu Q., Yuan Q., Chen M., Guo M., Huang H., Multicomponent Reactions with Cyclic Tertiary Amines Enabled by Facile C−N Bond Cleavage, Angew. Chem. Int. Ed., 56: 5101-5105 (2017).
[22] Ross S.D., Bruno J.J., Petersen R.C., Nucleophilic Displacement Reactions in Aromatic Systems. VII. The Ortho:Para Ratio in the Reactions of Nitrochlorobenzenes with Piperidine and with 1,4-diazabicyclo(2.2.2)octane, J. Am. Chem. Soc., 85: 2603-2607 (1963).
[23] Wang H.J., Wang Y., Csakai A.J., Earley W.G., Herr R.J., Efficient N-Arylation/Dealkylation of Electron Deficient Heteroaryl Chlorides and Bicyclic Tertiary Amines under Microwave Irradiation,J. Comb. Chem., 11: 355-363 (2009).
[24] Koyioni M., Manoli M., Koutentis P.A., The Reaction of DABCO with 4-Chloro-5H-1,2,3-Dithiazoles: Synthesis and Chemistry of 4-[N-(2-Chloroethyl)piperazin-1-yl]-5H-1,2,3-dithiazoles, J. Org. Chem., 81: 615-631 (2016).
[25] Yavari I., Bayat M.J., Ghazanfarpour-Darjani M., Synthesis of N-alkyl-N′-aryl-piperazines via Copper-Catalyzed C–N Bond Formation, Tetrahedron lett., 55: 5595-5596 (2014).
[26] Ghazanfarpour-Darjani M., Babapour-Kooshalshahi M., Mousavi-Safavi S.M., Akbari-Neyestani J., Khalaj M., Copper-Catalyzed Domino Addition–Cyclization Reaction between Terminal Alkynes, Carbon Disulfide, and Oxiranes, Synlett., 27: 259-261 (2016).
[27] Shahsavari F., Abbasi A., Ghazanfarpour-Darjani M., Ghafelebashi S.M., Daftari-Besheli M.,Synthesis of Allylbenzene Derivatives via sp3 C-H Bond Transformation of Toluene, Synlett., 28: 1646-1648 (2017).
[28] Khalaj M., Ghazanfarpour-Darjani M., Barat-Seftejani F., Nouri A., Novel Catalytic Three-Component Reaction between a Terminal Alkyne, Sulfonyl Azide, and O-Methyl Oxime, Synlett., 28: 1445-1448 (2017).
[29] Khalaj M., Ghazanfarpour-Darjani M., Talei Bavil Olyai M.R., Faraji Shamami S., Palladium Nanoparticles as Reusable Catalyst for the Synthesis of N-Aryl Sulfonamides under Mild Reaction Conditions, Journal of Sulfur Chemistry, 37: 211-222 (2016).