Palladium-catalyzed nucleophile-alkyne-α,β-unsaturated carbonyl coupling through tandem nucleopalladation and conjugate addition

Journal of Organic Chemistry

Volumn 61, Issue 7, 1996, Pages 2254-2255

  Wang, Zhong ^a   Lu, Xiyan ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000987232     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9522466     Document Type: Article

References (31)

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3. Posner, G. H. Org. React. 1972, 19, 1. Taylor, R. J. K. Synthesis 1985, 364. Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon: Oxford, 1992.
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16. Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581. Heck, R. F.; Nolley, J. P., Jr. J. Org. Chem. 1972, 37, 2320. For reviews, see: Heck, R. F. Org. React. 1982, 27, 345. Cabri, W.; Candiani, I. Acc. Chem. Res. 1993, 28, 2.
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20. The β-hydride elimination of an alkylmetal is a process in which the metal center accepts electron density from the β-hydride; see ref 6b.
21. Polar solvent and high concentration halides favor trans-halo-palladation which gives β-(Z)-halopropenoate derivatives; see ref 4b and: Ma, S.; Lu, X. J. Org. Chem. 1991, 56, 5120. Backvall, J.-E.; Nilsson, Y. I. M.; Gatti, R. G. P. Organometallics 1995, 14, 4242.
22. Polar solvent and high concentration halides favor trans-halo-palladation which gives β-(Z)-halopropenoate derivatives; see ref 4b and: Ma, S.; Lu, X. J. Org. Chem. 1991, 56, 5120. Backvall, J.-E.; Nilsson, Y. I. M.; Gatti, R. G. P. Organometallics 1995, 14, 4242.
23. In our previous work on palladium(II)-catalyzed cyclization of 4′-acetoxy-2′-butenyl 2-alkynoates, we found that even in the presence of a large amount of lithium acetate, chloropalladation products are formed in preference to acetoxypalladation products.
24. 2:LiX.3a =1:5: 20 ratio, LiBr gave a clean reaction producing 4a while LiCl resulted in the formation of 5a and Pd metal.
25. Cacchi, S. Pure Appl. Chem. 1990, 62, 713. Copéret, C.; Sugihara, T.; Wu, G.; Shimoyama, I.; Negishi, E.-I. J. Am. Chem. Soc. 1995, 117, 3422.
26. Cacchi, S. Pure Appl. Chem. 1990, 62, 713. Copéret, C.; Sugihara, T.; Wu, G.; Shimoyama, I.; Negishi, E.-I. J. Am. Chem. Soc. 1995, 117, 3422.
27. In Utimoto's work on palladium-catalyzed cyclization coupling of alkynoic acids with allyl halides, 3-butynoic acid also failed to give the cyclization product; see ref 4d.
28. Krafft, G. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1981, 103, 5459. Chan, D. M. T.; Marder, T. B.; Milstein, D.; Taylor, N. J. J. Am. Chem. Soc. 1987, 109, 6385.
29. Krafft, G. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1981, 103, 5459. Chan, D. M. T.; Marder, T. B.; Milstein, D.; Taylor, N. J. J. Am. Chem. Soc. 1987, 109, 6385.
30. There is strong NOE between two groups of allylic protons and no NOE between the phenyl group and the protons on lactone ring.
31. 2 (0.02 mmol), LiBr (2 mmol), and acrolein (5 mmol) in HOAc (5 mL) in 1 h at rt. Similar workup gave the coupled product.