[1]
Sagar A, Vidyacharan S, Sharada DSI. l2-promoted cross-dehydrogenative coupling of α-carbonyl aldehydes with alcohols for the synthesis of α-ketoesters. RSC Advances 2014; 4: 37047-50. [http://dx.doi.org/10.1039/C4RA06028H].
[2]
Liu C, Liu D, Lei AW. Recent advance of transition-metal catalyzed radical oxidative cross-coup. Acc Chem Res 2014; 47(12): 3459-70.
[3]
Barrett AGM, Graboski GG. Conjugated nitroalkenes: versatile intermediates in organic synthesis. Chem Rev 1986; 86: 751-62. [http://dx.doi.org/10.1021/cr00075a002].
[4]
Barrett AGM. Heterosubstituted nitroalkenes in synthesis. Chem Soc Rev 1991; 20: 95-127. [http://dx.doi.org/10.1039/cs9912000095].
[5]
Fioravanti S, Pellacani L, Tardella PA, Vergari MC. Facile and highly stereoselective one-pot synthesis of either (E)- or (Z)-nitro alkenes. Org Lett 2008; 10(7): 1449-51. [http://dx.doi.org/10.1021/ol800224k]. [PMID: 18302403].
[6]
Liu C, Liu D, Lei A. Recent advances of transition-metal catalyzed radical oxidative cross-couplings. Acc Chem Res 2014; 47(12): 3459-70. [http://dx.doi.org/10.1021/ar5002044]. [PMID: 25364854].
[7]
Yan G, Yang M. Recent advances in the synthesis of aromatic nitro compounds. Org Biomol Chem 2013; 11(16): 2554-66. [http://dx.doi.org/10.1039/c3ob27354g]. [PMID: 23443836].
[8]
Mąkosza M. Reactions of nucleophiles with nitroarenes: multifacial and versatile electrophiles. Chemistry 2014; 20(19): 5536-45. [http://dx.doi.org/10.1002/chem.201400097]. [PMID: 24687770].
[9]
Phillips AMF. Recent advances on the organocatalytic asymmetric Aza-Henry reaction. Curr Org Catal 2016; 3: 222-42.
[10]
Ono N. The Nitro Group in Organic Synthesis. Wiley & Sons: New York 2001. [http://dx.doi.org/10.1002/0471224480]
[11]
Mondal M, Bharadwaj SK, Bora U. O-Arylation with nitroarenes: metal-catalyzed and metal-free methodologies. New J Chem 2015; 39: 31-7. [http://dx.doi.org/10.1039/C4NJ01293C].
[12]
Manna S, Jana S, Saboo T, Maji A, Maiti D. Synthesis of (E)-nitroolefins via decarboxylative nitration using t-butylnitrite (t-BuONO) and TEMPO. Chem Commun (Camb) 2013; 49(46): 5286-8. [http://dx.doi.org/10.1039/c3cc41576g]. [PMID: 23636417].
[13]
Zarei M, Noroozizadeh E, Moosavi-Zare AR, Zolfigol MA. Synthesis of nitroolefins and nitroarenes under mild conditions. J Org Chem 2018; 83(7): 3645-50. [http://dx.doi.org/10.1021/acs.joc.7b03289]. [PMID: 29504403].
[14]
Wang XW, Cui HF, Wang HF. Yang, Y.Q.; Zhao, G.; Zhu, S.Z. A novel method for the synthesis of 3-fluoro-4-aryl-2-pyridone via unprecedented denitration. Tetrahedron 2011; 67: 2468-73. [http://dx.doi.org/10.1016/j.tet.2011.01.047].
[15]
Nakano T, Miyazaki K, Kamimura A. Preparation of 2,3-dihydrofurans via a double allylic substitution reaction of allylic nitro compounds. J Org Chem 2014; 79(17): 8103-9. [http://dx.doi.org/10.1021/jo5013042]. [PMID: 25093914].
[16]
Reddy MK, Mallik S, Ramakrishna I, Baidya M. Nitrosocarbonyl−Henry and denitration cascade: synthesis of α-ketoamides and α-keto oximes. Org Lett 2017; 19(7): 1694-7. [http://dx.doi.org/10.1021/acs.orglett.7b00482]. [PMID: 28286956].
[17]
Zhao K, Shu T, Jia J, Raabe G, Enders D. An organocatalytic Mannich/denitration reaction for the asymmetric synthesis of 3-ethylacetate-substitued 3-amino-2-oxindoles: formal synthesis of AG-041R. Chemistry 2015; 21(10): 3933-6. [http://dx.doi.org/10.1002/chem.201406422]. [PMID: 25630891].
[18]
Elagamy A, Shaw R, Panwar R. Shally.; Ram, V.J.; Pratap, R. Shally, Ram, V.J. and Pratap, R. Synthesis of highly functionalized spirobutenolides via a nitroalkane-mediated ring contraction of 2-oxobenzo[h]chromenes through denitration. J Org Chem 2019; 84(3): 1154-61. [http://dx.doi.org/10.1021/acs.joc.8b02257]. [PMID: 30652867].
[19]
Yan H, Yang SZ, Gao X, et al. Iron (II)-catalyzed denitration reaction: synthesis of 3-methyl-2-arylimidazo[1,2-a]pyridine derivatives from aminopyridines and 2-methylnitroolefins. Synlett 2012; 23: 2961-4. [http://dx.doi.org/10.1055/s-0032-1317685].
[20]
Yan H, Wang YL, Pan CM, Zhang H, Yang SZ, Ren XY. Li, J. and Huang, G.S. Iron(III)-catalyzed denitration reaction: one-pot three-component synthesis of imidazo[1,2-a]pyridine derivatives. Eur J Org Chem 2014; 2754-63. [http://dx.doi.org/10.1002/ejoc.201301658].
[21]
Zhang N, Quan Z-J, Wang X-C. Nickel-catalyzed denitrated coupling reaction of nitroalkenes with aliphatic and aromatic alkenes. Adv Synth Catal 2016; 358: 3179-83. [http://dx.doi.org/10.1002/adsc.201600586].
[22]
Keshari T, Kapoorr R, Yadav LDS. Silver-catalyzed denitrative sulfonylation of β-nitrostyrenes: A convenient approach to (E)-vinyl sulfones. Eur J Org Chem 2016; 2695-9. [http://dx.doi.org/10.1002/ejoc.201600237].
[23]
Ma JJ, Yi WB, Lu GP, Cai C. Decarboxylative and denitrative trifluoromethylation for the synthesis of Cvinyl-CF3 compounds with Togni (II) reagent. Adv Synth Catal 2015; 357: 3447-52. [http://dx.doi.org/10.1002/adsc.201500631].
[24]
Huang P, Li YM, Fu XM, et al. Silver(I)-catalyzed denitrative trifluoromethylation of β-nitrostyrenes with CF3SO2Na. Tetrahedron Lett 2016; 57: 4705-8. [http://dx.doi.org/10.1016/j.tetlet.2016.09.016].
[25]
Xue J-F, Zhou S-F, Liu Y-Y, Pan X, Zou J-P, Asekun OT. Manganese(III)-mediated alkenyl Csp2-P bond formation from the reaction of β-nitrostyrenes with dialkyl phosphites. Org Biomol Chem 2015; 13(17): 4896-902. [http://dx.doi.org/10.1039/C5OB00404G]. [PMID: 25812140].
[26]
Yuan J-W, Yang L-R, Mao P, Qu L-B. Silver-catalyzed synthesis of 2-arylvinylphosphonates by cross-coupling of β-nitrostyrenes with H-phosphites. RSC Advances 2016; 6: 87058-65. [http://dx.doi.org/10.1039/C6RA19002B].
[27]
Tang L, Wen LX, Sun T, et al. Solvent-controlled copper-catalyzed radical decarboxylative coupling for alkenyl Csp2-P bond formation. Asian J Org Chem 2017; 6: 1683-92. [http://dx.doi.org/10.1002/ajoc.201700434].
[28]
Sagar A, Babu VN. Dey, A.; Sharada, D.S. I2-promoted denitration strategy: one-pot three component synthesis of pyrrole-fused benzoxazines. Tetrahedron Lett 2015; 56: 2710-3. [http://dx.doi.org/10.1016/j.tetlet.2015.04.011].
[29]
Bakthadoss M, Sivakumar N, Devaraj A, Kumar PV. Synthesis of highly diversified 1,2,3-triazole derivatives via domino [3+2] azide cycloaddition and denitration reaction sequence. RSC Advances 2015; 5: 93447-51. [http://dx.doi.org/10.1039/C5RA14195H].
[30]
Lei C, Gao ZH, Shao XS, Xu XY, Li Z. Synthesis of trisubstituted isoxazoles from nitroenamines and aromatic aldehydes. Chin J Chem 2017; 35: 1517-21. [http://dx.doi.org/10.1002/cjoc.201700170].
[31]
Yadav AK, Singh KN. Metal-free denitrative arylation of β-nitrostyrenes using benzoyl peroxide: an easy access to trans-stilbenes. New J Chem 2017; 41: 14914-7. [http://dx.doi.org/10.1039/C7NJ02997G].
[32]
Kumar S, Singh R, Singh KN. AIBN-Initiated denitrative cross-coupling reactions of β-nitrostyrenes with sulfonyl hydrazides/disulfides: a metal-free approach towards vinyl sulfones. Asian J Org Chem 2018; 7: 359-62. [http://dx.doi.org/10.1002/ajoc.201700632].
[33]
Aegurla B, Peddinti RK. Metal-free sulfonylation of α,β-conjugated systems by using sulfonyl hydrazides. Asian J Org Chem 2018; 7: 946-54. [http://dx.doi.org/10.1002/ajoc.201700696].
[34]
Kielmann M, Flanagan KJ, Norvaiša K, Intrieri D, Senge MO. Synthesis of a family of highly substituted porphyrin thioethers via nitro displacement in 2,3,7,8,12,13,17,18- octaethyl-5,10,15,20-tetranitroporphyrin. J Org Chem 2017; 82(10): 5122-34. [http://dx.doi.org/10.1021/acs.joc.7b00328]. [PMID: 28452490].
[35]
Devi ES, Alanthadka A, Nagarajan S, Sridharan V, Maheswari CU. Metal-free, base catalyzed oxidative amination and denitration reaction: Regioselective synthesis of 3-arylimidazo[1,2-a]pyridines. Tetrahedron Lett 2018; 59: 3485-9. [http://dx.doi.org/10.1016/j.tetlet.2018.08.024].
[36]
Reddy RJ, Waheed M, Karthik T, Shankar A. Efficient synthesis of 4,5-disubstituted-2H-1,2,3-triazoles from nitroallylic derivatives via cycloaddition-denitration process. New J Chem 2018; 42: 980-7. [http://dx.doi.org/10.1039/C7NJ03292G].
[37]
Hong GF, Yuan JW, Dong ZH, Xiao YM, Mao P, Qu LB. Metal-free synthesis of (E)-vinyl sulfones via denitrative coupling reactions of β-nitrostyrenes with sodium sulfinates. Phosphorus Sulfur Silicon Relat Elem 2018; 193: 771-9. [http://dx.doi.org/10.1080/10426507.2018.1513518].
[38]
Zuo Z, Ahneman DT, Chu L, Terrett JA, Doyle AG, MacMillan DWC. Dual catalysis. Merging photoredox with nickel catalysis: coupling of α-carboxyl sp3-carbons with aryl halides. Science 2014; 345(6195): 437-40. [http://dx.doi.org/10.1126/science.1255525]. [PMID: 24903563].
[39]
Davies J, Booth SG, Essafi S, Dryfe RAW, Leonori D. Visible-light-mediated generation of nitrogen-centered radicals: metal-free hydroimination and iminohydroxylation cyclization reactions. Angew Chem Int Ed Engl 2015; 54(47): 14017-21. [http://dx.doi.org/10.1002/anie.201507641]. [PMID: 26412046].
[40]
Prier CK, Rankic DA, MacMillan DWC. Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis. Chem Rev 2013; 113(7): 5322-63. [http://dx.doi.org/10.1021/cr300503r]. [PMID: 23509883].
[41]
Chen J, Cen J, Xu XL, Li XN. The application of heterogeneous visible light photocatalysts in organic synthesis. Catal Sci Technol 2016; 6: 349-62. [http://dx.doi.org/10.1039/C5CY01289A].
[42]
Zhang N, Quan ZJ, Zhang Z, Da YX, Wang XC. Synthesis of stilbene derivatives via visible-light-induced cross-coupling of aryl diazonium salts with nitroalkenes using -NO2 as a leaving group. Chem Commun (Camb) 2016; 52(99): 14234-7. [http://dx.doi.org/10.1039/C6CC08182G]. [PMID: 27872921].
[43]
Tripathi S, Kapoor R, Yadav LDS. Visible light activated radical denitrative benzoylation of β-Nitrostyrenes: A photocatalytic approach to chalcones. Adv Synth Catal 2018; 360: 1407-13. [http://dx.doi.org/10.1002/adsc.201701559].
[44]
Tripathi S, Yadav LDS. Visible-light-enabled denitrative carboxylation of β-nitrostyrenes: a direct photocatalytic approach to cinnamic acids. New J Chem 2018; 42: 3765-9. [http://dx.doi.org/10.1039/C7NJ04578F].
[45]
Wang HL, Yu AJ, Cao AJ, Chang JB, Wu YJ. First palladium-catalyzed denitrated coupling reaction of nitroarenes with phenols. Appl Organomet Chem 2013; 27: 611-4. [http://dx.doi.org/10.1002/aoc.3043].
[46]
Maity T, Saha D, Bhunia S, Brandão P, Dasa S, Koner S. A family of ligand and anion dependent structurally diverse Cu(II) Schiff-base complexes and their catalytic efficacy in O–arylation reaction in ethanolic medium. RSC Advances 2015; 5: 82179-91. [http://dx.doi.org/10.1039/C5RA14758A].
[47]
Xu XL, Feng THJB, Xu HJ. Nano-CuI catalyzed cross-coupling reaction of phenols with nitroarenes. Youji Huaxue 2016; 36: 1021-7. [http://dx.doi.org/10.6023/cjoc201603011].
[48]
Begum T, Mondal M, Borpuzari MP, Kar R, Gogoi PK, Bora U. Palladium-on-carbon-catalyzed coupling of nitroarenes with phenol: biaryl ether synthesis and evidence of an oxidative- addition-promoted mechanism. Eur J Org Chem 2017; 3244-8. [http://dx.doi.org/10.1002/ejoc.201700639].
[49]
Zamiran F, Ghaderi A. Nickel-catalyzed denitrative etherification of activated nitrobenzenes. J Iran Chem Soc 2019; 16: 293-9. [http://dx.doi.org/10.1007/s13738-018-1510-0].
[50]
Zheng X, Ding J, Chen J, Gao W, Liu M, Wu H. The coupling of arylboronic acids with nitroarenes catalyzed by rhodium. Org Lett 2011; 13(7): 1726-9. [http://dx.doi.org/10.1021/ol200251x]. [PMID: 21375321].
[51]
Zhang JL, Chen JX, Liu MC, Zheng XW, Ding JC, Wu HY. Ligand-free copper-catalyzed coupling of nitroarenes with arylboronic acids. Green Chem 2012; 14: 912-6. [http://dx.doi.org/10.1039/c2gc16539b].
[52]
Peng DP, Yu AJ, Wang HL, Wu YJ, Chang JBA. 2,2′-bipyridine-palladacycle catalyzed the coupling of arylboronic acids with nitroarenes. Tetrahedron 2013; 69: 6884-9. [http://dx.doi.org/10.1016/j.tet.2013.05.112].
[53]
Bahekar SS, Sarkate AP, Wadhai VM, Wakte PS, Shinde DB. CuI catalyzed C-S bond formation by using nitroarenes. Catal Commun 2013; 41: 123-5. [http://dx.doi.org/10.1016/j.catcom.2013.07.019].
[54]
Rostami A, Rostami A, Ghaderi A. Copper-catalyzed thioetherification reaction of alkyl halides, triphenyltin chloride and arylboronic acids with nitroarenes in the presence of sulfur sources. J Org Chem 2015; 80(17): 8694-704. [http://dx.doi.org/10.1021/acs.joc.5b01248]. [PMID: 26272238].
[55]
Moghaddama FM, Pourkaveh R. Nano cobalt ferrite catalyzed coupling reaction of nitroarene and alkyl halide: an odorless and ligand-free route to unsymmetrical thioether synthesis. Catal Commun 2017; 94: 33-7. [http://dx.doi.org/10.1016/j.catcom.2017.02.009].
[56]
Tian H, Cao AJ, Qiao LJYuJ, Chang JB, Wu YJ. First palladium-catalyzed denitrated coupling of nitroarenes with sulfinates. Tetrahedron 2014; 70: 9107-12. [http://dx.doi.org/10.1016/j.tet.2014.09.087].
[57]
Yadav MR, Nagaoka M, Kashihara M, et al. The Suzuki−Miyaura coupling of nitroarenes. J Am Chem Soc 2017; 139(28): 9423-6. [http://dx.doi.org/10.1021/jacs.7b03159]. [PMID: 28678486].
[58]
Kashihara M, Yadav MR, Nakao Y. Reductive denitration of nitroarenes. Org Lett 2018; 20(6): 1655-8. [http://dx.doi.org/10.1021/acs.orglett.8b00430]. [PMID: 29488770].
[59]
Inoue F, Kashihara M, Yadav MR, Nakao Y. Buchwald–Hartwig amination of nitroarenes. Angew Chem Int Ed Engl 2017; 56(43): 13307-9. [http://dx.doi.org/10.1002/anie.201706982]. [PMID: 28857476].
[60]
Yu XC, Li B, Yu BH, Xu Q. Efficient synthesis of unsymmetrical diaryl thioethers via TBAF-mediated denitrative substitution of nitroarenes with PhSTMS under mild and neutral conditions. Chin Chem Lett 2013; 24: 605-8. [http://dx.doi.org/10.1016/j.cclet.2013.04.011].
[61]
Nguyen TB, Retailleau P. DIPEA-promoted reaction of 2-nitrochalcones with elemental sulfur: an unusual approach to 2-benzoylbenzothiophenes. Org Lett 2017; 19(18): 4858-60. [http://dx.doi.org/10.1021/acs.orglett.7b02321]. [PMID: 28840729].
[62]
Moore TM, Akula MR, Collier L, Kabalka GW. A rapid microfluidic synthesis of [18F]fluoroarenes from nitroarenes. Appl Radiat Isot 2013; 71(1): 47-50. [http://dx.doi.org/10.1016/j.apradiso.2012.09.013]. [PMID: 23085551].
[63]
Kuduk SD, DiPardo RM, Bock MG. Tetrabutylammonium salt induced denitration of nitropyridines: Synthesis of fluoro-, hydroxy-, and methoxypyridines. Org Lett 2005; 7(4): 577-9. [http://dx.doi.org/10.1021/ol047688v]. [PMID: 15704898].
[64]
Sarkate AP, Bahekar SS, Wadhai VM, Ghandge GN, Wakte PS, Shinde DB. Microwave-assisted synthesis of nonsymmetrical aryl ethers using nitroarenes synthesis of nonsymmetrical aryl ethers. Synlett 2013; 24: 1513-6. [http://dx.doi.org/10.1055/s-0033-1338869].
Download PDF Flyer