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Palladium-catalyzed cascade reactions of benzyl halides with N,N-diallyl-p-toluenesulfonamide

  • Liansheng Wang EMAIL logo , Yi Pan and Hongwen Hu
Published/Copyright: August 1, 2012

Abstract

Reaction of N,N-diallyl-p-toluenesulfonamide 1 with benzyl halides 2 in the presence of a palladium catalyst afforded a series of novel dihydropyrroles 3 in moderate yields. A palladium-catalyzed self-cyclization reaction of the diene 1 may take place to give a cyclic dihydropyrrole 4 during the reaction. It is proposed that the cyclic products 4 are formed via a palladium-catalyzed cascade cyclization-coupling process. Reaction of phenyl iodide 5 with 1 in the same condition afforded normal Heck vinylation products 6.


Corresponding author: Liansheng Wang, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, P.R. China; and School of Chemistry and Materials Science, Hubei Engineering University, Xiaogan 432000, P.R. China

References

de Meijere, A.; Meyer, F. E. Fine feathers make fine birds: the heck reaction in modern garb. Angew. Chem. Int. Ed. 1995, 33, 2379–2411.10.1002/anie.199423791Search in Google Scholar

Furstner, A.; Langemann, K. A concise total synthesis of dactylol via ring closing metathesis. J. Org. Chem. 1996, 61, 8746–8749.10.1021/jo961600cSearch in Google Scholar PubMed

Furstner, A.; Muller, T. Efficient total syntheses of resin glycosides and analogues by ring-closing olefin metathesis. J. Am. Chem. Soc. 1999, 121, 7814–7821.10.1021/ja991361lSearch in Google Scholar

Goj, L. A.; Cisneros, G. A.; Yang, W. T.; Widenhoefer, W. A. Dramatic effect of homoallylic substitution on the rate of palladium-catalyzed diene cycloisomerization. J. Organomet. Chem. 2003, 687, 498–507.10.1016/j.jorganchem.2003.09.046Search in Google Scholar

Grigg, R. Heterocycle synthesis by palladium catalysed cyclisation-anion capture processes: a powerful new strategy. J. Heterocycl. Chem. 1994, 31, 631–639.10.1002/jhet.5570310305Search in Google Scholar

Grigg, R.; Koppen, I.; Rasoarini, M.; Sridharan, V. Synthesis of spiro- and fused heterocycles by palladium catalysed carbo- and heteroannulation cascades of allenes. Chem. Commun. 2001, 11, 964–965.10.1039/b102046nSearch in Google Scholar

Heck, R. F. Acylation, methylation, and carboxyalkylation of olefins by group VIII metal derivatives. J. Am. Chem. Soc. 1968, 90, 5518–5526.10.1021/ja01022a034Search in Google Scholar

Heck, R. F. Palladium-catalyzed vinylation of organic halides. Org. React. 1982, 27, 345–390.10.1002/0471264180.or027.02Search in Google Scholar

Hu, Y. M.; Zhou, J.; Long, X. T.; Han, J. L.; Zhu, C. J.; Pan, Y. Palladium-catalyzed cascade reactions of benzyl halides with N-allyl-N-(2-butenyl)-p-toluenesulfonamide. Tetrahedron Lett. 2003, 44, 5009–5010.10.1016/S0040-4039(03)01177-8Search in Google Scholar

Lee, C. W.; Oh, K. S.; Kim, K. S.; Ahn, K. H. Suppressed β-hydride elimination in palladium-catalyzed cascade cyclization-coupling reactions: an efficient synthesis of 3-arylmethylpyrrolidines. Org. Lett. 2000, 2, 1213–1216.10.1021/ol0056426Search in Google Scholar PubMed

Miura, K.; Hondo, T.; Nakagawa, T.; Takahashi, T.; Hosomi, A. Acid-catalyzed cyclization of vinylsilanes bearing an amino group: stereoselective synthesis of pyrrolidines. Org. Lett. 2000, 2, 385–388.10.1021/ol991341oSearch in Google Scholar PubMed

Negishi, E.; Coperet, C.; Ma, S.; Liou, S. Y.; Liu, F. Cyclic carbopalladation: a versatile synthetic methodology for the construction of cyclic organic compounds. Chem. Rev. 1996, 96, 365–394.10.1021/cr950020xSearch in Google Scholar PubMed

Pan, Y.; Zhang, Z. Y.; Hu, H. W. Vinylation of benzylic quaternary ammonium-salts catalyzed by palladium. Synthesis1995, 3, 245–247.10.1055/s-1995-3911Search in Google Scholar

Pernerstorfer, J.; Schuster, M.; Blechert, S. Cyclisation/cleavage of macrocycles by ring-closing metathesis on solid support – conformational studies. Chem. Commun. 1997, 20, 1949–1950.10.1039/a704976eSearch in Google Scholar

Takacs, J. M.; Zhu, J. Y.; Chandramouli, S. Catalytic palladium-mediated tetraene carbocyclizations: the cycloisomerizations of acyclic tetraenes to cyclized trienes. J. Am. Chem. Soc. 1992, 114, 773–774.10.1021/ja00028a061Search in Google Scholar

Tsuji, J. Palladium Reagents and Catalysis: Innovations in Organic Synthesis; Wiley: Chichester, 1995.Search in Google Scholar

Wang, L.S.; Pan, Y.; Jiang, X.; Hu, H. W. Palladium catalyzed reaction of α-chloromethyl-naphthalene with olefins. Tetrahedron Lett. 2000, 41, 725–727.10.1016/S0040-4039(99)02154-1Search in Google Scholar

Wang, X.; Chakrapani, H.; Stengone, C. N.; Widenhoefer, R. A. Synthesis of carbobicyclic compounds via palladium-catalyzed cyclization/hydrosilylation: evidence for reversible silylpalladation. J. Org. Chem. 2001, 66, 1755–1760.10.1021/jo001438kSearch in Google Scholar PubMed

Wu, G. Z.; Lamaty, F.; Negishi, E. Metal-promoted cyclization 26: palladium-catalyzed cyclization of benzyl halides and related electrophiles containing alkenes and alkynes as a novel route to carbocycles. J. Org. Chem. 1989, 54, 2507–2508.10.1021/jo00272a006Search in Google Scholar

Yuan, K. J.; Xia, P. Organic Heterocyclic Chemistry; People's Medical Publishing House: Beijing, 1984.Search in Google Scholar

Zhang, Z. Y.; Pan, Y.; Hu, H. W.; Kao, T. Y. A facile approach to 2-arylethylamines via polymeric palladium catalyst. Synth. Commun. 1990, 20, 3563–3574.10.1080/00397919008051600Search in Google Scholar

Received: 2012-05-30
Accepted: 2012-06-12
Published Online: 2012-08-01
Published in Print: 2012-08-01

©2012 Walter de Gruyter GmbH & Co. KG, Berlin/Boston

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