Application of 1-(α-aminobenzyl)-2-naphthols as air-stable ligands for pd-catalyzed Mizoroki-Heck coupling reaction

Synthetic Communications

Volumn 42, Issue 12, 2012, Pages 1778-1785

  Chaudhary, Anju R ^a   Bedekar, Ashutosh V ^a  

^a M S UNIVERSITY OF BARODA   (India)

Author keywords

1 ( Aminobenzyl) 2 naphthols; Mizoroki Heck; Phosphine free ligands

Indexed keywords

BROMINE DERIVATIVE; CHLORIDE; LIGAND; MANNICH BASE; NAPHTHOL DERIVATIVE; PALLADIUM;

ARTICLE; ARYLATION; CATALYSIS; CONTROLLED STUDY; HECK REACTION;

EID: 84857617166     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.544439     Document Type: Article

References (35)

1. Mizoroki, T.; Mori, K.; Ozaki, A. Arylation of olefins with aryl iodide catalyzed by palladium. Bull. Chem. Soc. Jpn. 1971, 44, 581.
2. Heck, R. F.; Nolly, J. P. Palladium-catalyzed vinylic hydrogen substitution reactions with aryl, benzyl, and styryl halides. J. Org. Chem. 1972, 37, 2320-2322.
3. Heck, R. F. Palladium-catalyzed reactions of organic halides with olefins. Acc. Chem. Res. 1979, 12, 146-151.
4. De Meijere, A.; Meyer, F. E. Fine feathers make fine birds: The Heck reaction in modern garb. Angew. Chem. Int. Ed. 1994, 33, 2379-2411. (Pubitemid 24977304)
5. Beletskaya, I. P.; Cheprakov, A. V. The Heck reaction as a sharpening stone of palladium catalysis. Chem. Rev. 2000, 100, 3009-3066.
6. Bedford, R. B.; Cazin, C. S. J.; Holder, D. The development of palladium catalysts for C-C and C-heteroatom bond-forming reactions of aryl chloride substrates. Coord. Chem. Rev. 2004, 248, 2283-2321.
7. Amatore, C.; Jutand, A. Anionic Pd(0) and Pd(II) intermediates in palladium-catalyzed Heck and cross-coupling reactions. Acc. Chem. Res. 2000, 33, 314-321.
8. Herrmann, W. A. N-Heterocyclic carbenes: A new concept in organometallic catalysis. Angew. Chem. Int. Ed. 2002, 41, 1290-1309. (Pubitemid 34437411)
9. Hermann, W. A.; Ofele, K.; von Preysing, D.; Schneider, S. K. Phospha-palladacycles and N-heterocyclic carbene palladium complexes: Efficient catalysts for C-C coupling reactions. J. Organomet. Chem. 2003, 687, 229-248.
10. Farina, V. High-turnover palladium catalysts in cross-coupling and Heck chemistry: A critical overview. Adv. Synth. Catal. 2004, 346, 1553-1582. (Pubitemid 40142618)
11. Botella, L.; Nájera, C. Mono- and β, β-double-Heck reactions of a,b-unsaturated carbonyl compounds in aqueous media. J. Org. Chem. 2005, 70, 4360-4369. (Pubitemid 40734148)
12. Eisnor, C. R.; Gossage, R. A.; Yadav, P. N. Oxazoline chemistry, part 11: Synthesis of natural and synthetic isoflavones, stilbenes, and related species via C-C bond formation promoted by a Pd-ozaxoline complex. Tetrahedron 2006, 62, 3395-3401.
13. Mino, T.; Shirae, Y.; Sasai, Y.; Sakemoto, M.; Fujita, T. Phosphine-free palladium catalyzed Mizoroki-Heck reaction using hydrazone as a ligand. J. Org. Chem. 2006, 71, 6834-6839. (Pubitemid 44645659)
14. Herrmann, W. A.; Elison, M.; Fischer, J.; Kosher, C.; Artus, G. R. J. Metal complexes of N-heterocyclic carbenes-A new structural principle for catalysts in homogeneous catalysis. Angew. Chem., Int. Ed. 1995, 34, 2371-2374.
15. Littman, J. B.; Brode, W. R. Condensations of secondary amines with aldehydes and naphthols. J. Am. Chem. Soc. 1930, 52, 1655-1659.
16. Paul, N. K.; Dietrich, L.; Jha, A. Convenient synthesis of 1-arylmethyl-2-naphthols. Synth. Commun. 2007, 37, 877-888. (Pubitemid 46328388)
17. Betti, M. Condensation between β-naphthol, aldehydes, and amines. Gazz. Chim. Ital. 1900, 30, 310-316.
18. Cardellicchio, C.; Ciccarella, G.; Naso, F.; Schingaro, E.; Scordari, F. The Betti base: Absolute configuration and routes to a family of related chiral nonracemic bases. Tetrahedron: Asymmetry 1998, 9, 3667-3675. (Pubitemid 28529730)
19. Cimarelli, C.; Mazzanti, A.; Palmieri, G.; Volpini, E. Solvent-free asymmetric aminoalkylation of electron-rich aromatic compounds: Stereoselective synthesis of aminoalkylnaphthols by crystallization-induced asymmetric transformation. J. Org. Chem. 2001, 66, 4759-4765. (Pubitemid 32861787)
20. Szatmári, I.; Martinek, T. A.; Lázár, L.; Fülöp, F. Substituent effects in the ring-chain tautomerism of 1,3-diaryl-2,3-dihydro-1H-naphth[1.2-e][1.3]oxazines. Tetrahedron 2003, 59, 2877-2884. (Pubitemid 36419549)
21. Szatmári, I.; Fülöp, F. Synthesis and transformations of 1-(α-aminobenzyl)-2-naphthol derivatives. Curr. Org. Synth. 2004, 1, 155-165.
22. Palmieri, G. A practical o-hydroxybenzylamines-promoted enantioselective addition of dialkylzinc to aldehydes with asymmetric amplification. Tetrahedron: Asymmetry 2000, 11, 3361-3373.
23. Liu, D.-X.; Zhang, L.-C.; Wang, Q.; Da, C.-S.; Xin, Z.-Q.; Wang, R.; Choi, M. C. K. Chan, A. S. C. The application of chiral aminonaphthols in the enantioselective addition of diethylzinc to aryl aldehydes. Org. Lett. 2001, 3, 2733-2735. (Pubitemid 33625284)
24. Lu, J.; Xu, X.; Wang, S.; Wang, C.; Hu, Y.; Hu, H. Novel preparation of non-racemic 1-[α-(1-azacycloalkyl)benzyl]-2-naphthols from Betti base and their application as chiral ligands in the asymmetric addition of diethylzinc to aryl aldehydes. J. Chem. Soc., Perkin. Trans. 1, 2002, 2900-2903.
25. Lu, J.; Xu, X.; Wang, C.; He, J.; Hu, Y.; Hu, H. Synthesis of chiral ligands derived from the Betti base and their use in the enantioselective addition of diethylzinc to aromatic aldehydes. Tetrahedron Lett. 2002, 43, 8367-8369. (Pubitemid 35223375)
26. Cimarelli, C.; Palmieri, G.; Volpini, E. A practical stereoselective synthesis of secondary and tertiary aminonaphthols: Chiral ligands for enantioselective catalysts in the addition of diethylzinc to benzaldehyde. Tetrahedron: Asymmetry 2002, 13, 2417-2426. (Pubitemid 35356475)
27. Szatmári, I.; Sillanpää, R.; Fülöp, F. Microwave-assisted, highly enantioselective addition of diethylzinc to aromatic aldehydes catalyzed by chiral aminonaphthols. Tetrahedron: Asymmetry 2008, 19, 612-617.
28. Winter, W.; Langjahr, U.; Meier, H.; Merkuschew, J.; Juriew, J. Photochemie des 1,3,5-tristyrylbenzols. Chem. Ber. 1984, 117, 2452-2463.
29. Díez-Barra, E.; García-Martínez, J. C.; Merino, S.; del Rey, R.; Rodríguez-López, J.; Sánchez-Verdú, P.; Tejedac, J. Synthesis, characterisation, and optical response of dipolar and non-dipolar poly(phenylenevinylene)dendrimers. J. Org. Chem. 2001, 66, 5664-5670. (Pubitemid 32878487)
30. Dawood, K. M. Microwave-assisted Suzuki-Miyaura and Heck-Mizoroki cross-coupling reactions of aryl chlorides and bromides in water using stable benzothiazole-based palladium(II) precatalysts. Tetrahedron 2007, 63, 9642-9651. (Pubitemid 47238976)
31. Heynekamp, J. J.; Weber, W. M.; Hunsaker, L. A.; Gonzales, A. M.; Orlando, R. A.; Deck, L. M.; Van der Jagt, D.L. Substituted trans-stilbenes, including analogues of the natural product resveratrol, inhibit the human tumor necrosis factor α-induced activation of transcription factor nuclear factor κB. J. Med. Chem. 2006, 49, 7182-7189. (Pubitemid 44886003)
32. Alacid, E.; Najera, C. P. Palladium-catalyzed cross-coupling reactions of potassium alkenyltrifuloroborates with organic halides in aqueous media. J. Org. Chem. 2009, 74, 2321-2327.
33. Wan, P.; Davis, M. J.; Teo, M. A. Photoaddition of water and alcohols to 3-nitrostyrenes: Structure-reactivity and solvent study. J. Org. Chem. 1989, 54, 1354-1359.
34. Lansky, A.; Reiser, O.; De Meijere, A. Highly efficient alkene-alkene coupling reactions with vicinal dibromides. Synlett 1990, 7, 405-407.
35. Cella, R.; Stefani, H. A. Ultrasound-assisted synthesis of Z and E-stilbenes by Suzuki cross-coupling reactions of organotellurides with potassium organotrifluoroborate salts. Tetrahedron 2006, 62, 5656-5662. (Pubitemid 43668797)