Palladium-catalyzed [4+2] cross-benzannulation reaction of conjugated enynes with diynes and triynes

Journal of the American Chemical Society

Volumn 121, Issue 27, 1999, Pages 6391-6402

  Gevorgyan, Vladimir ^a,b   Takeda, Akira ^a   Homma, Miyako ^a   Sadayori, Naoki ^a   Radhakrishnan, Ukkiramapandian ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; BENZENE; BENZENE DERIVATIVE; DEUTERIUM; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS; STEREOSPECIFICITY;

EID: 0033553988     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990749d     Document Type: Article

References (53)

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26. The structure of para-oriented 8d was unambiguously confirmed by 500 MHz NOE- and COLOC NMR analyses. See Supporting Information (S28-S32).
27. Excess enyne 3a underwent homo-dimerization, affording 4a, see also footnote c, Table 1.
28. 9b we found that Pd(0) complexes, bulky phosphine ligands combinations (4-10-fold excess of phosphine ligands with respect to Pd content), were rather more thermally stable than Pd(0) complexes alone.
29. Both triple bonds of 13e exhibited rather similar reactivities toward 4-substituted enyne Sa, as well. Accordingly, trisubstituted benzenes 14k and 15k were obtained in 36% and 39%, respectively.
30. Preliminary low level ab initio computations revealed that the triple bond, attached to the TMS group, of unsymmetrical diyne 13f and of triyne 16g is more electron-rich than the others.
31. π-Propargyl palladium complexes have been recently isolated and fully characterized. See: (a) Ogoshi, S.; Tsutsumi, K.; Kurosawa, H. J. Organomet. Chem. 1995, 493, C19. (b) Ogoshi, S.; Tsutsumi, K.; Ooi, M.; Kurosawa, H. J. Am. Chem. Soc. 1995, 117, 10415.
32. π-Propargyl palladium complexes have been recently isolated and fully characterized. See: (a) Ogoshi, S.; Tsutsumi, K.; Kurosawa, H. J. Organomet. Chem. 1995, 493, C19. (b) Ogoshi, S.; Tsutsumi, K.; Ooi, M.; Kurosawa, H. J. Am. Chem. Soc. 1995, 117, 10415.
33. The coordination of palladium to propargyl group in the intermediate 37 is supported not only by the exclusive formation of a sole regioisomer 24 but also by the fact that simple alkynes, such as acetylene and its alkyl, aryl-, halo-, and cyanoderivatives which do not possess such an additional alkynyl group, do not act as enynophiles in the mentioned reaction at all. Accordingly, an alternative explanation for remarkably high reactivity of diynes in terms of steric effects is discounted by the observation that acetylene itself did not act as an enynophile in that reaction.
34. This type of six-membered strained cyclic cumulene has been proposed as an intermediate in the dehydro Diels-Alder cycloadditions, (a) For review see: Johnson, R. P. Chem. Rev. 1989, 89, 1111. (b) See also ref 8.
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41. Ester- 10j,k, and cyano-containing enynes 101,m were synthesized from the corresponding alkynyl ketones via Horner-Wadsworth-Emmons procedure, see: Rathke, M. W.; Nowak, M. J. Org. Chem. 1985, 50, 2624.
42. 2O.
43. 29 via Pd-catalyzed hydrostannation-deuteriodestannation (with DClaq) sequence. For Pd-catalyzed hydrostannation of diynes, see: Zhang, H. X.; Guibé, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857.
44. 20c
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52. 32b sequence. See: (a) Patel, G. N. J. Polym. Sci. Pol. Phys. Ed. 1979, 17, 1591. (b) Alberts, A. H. Recl. Trav. Chim. Pays-Bas 1989, 108, 242.
53. 1H NMR and GLC analyses, isolated yield) in a 5 mmol scale under the mentioned reaction conditions.