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3
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0031046817
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(a) Terao, Y.; Wakui, H.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2001, 123, 10407.
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0141856128
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Pd-catalyzed reaction of 1,1-disubstituted 3-phenyl-2-propyn-1-ols with alkenes: Nishimura, T.; Araki, H.; Maeda, Y.; Uemura, S. Org. Lett. 2003, 5, 2997.
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25
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27644472986
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note
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2-sp bonds is known. The reaction may proceed via either in situ generation of terminal alkynes or β-carbon elimination; see refs 4a,b and the relevant literature cited therein.
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-
-
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26
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27644563378
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note
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2 is considered to be due to its better ability to form the alkoxy complex. This resembles transmetalation with arylboronic acids.
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-
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29
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27644541731
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note
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2O or via H-D exchange of the starting alcohol.
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30
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27644558053
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note
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The reaction occurred only to a minor extent to give 10% of 2ap and completely stopped within 1 h. No cross-coupling with the terminal alkyne as well as its homocoupling was observed. However, the origin of the inhibiting effect is not clear at the present stage.
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33
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27644511138
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Of the expected cyclization products, only 3ap is known. Interestingly, it was described that the furan afforded fluorescent yellow-green needles, while the synthesis was rather tedious: Filler, R.; Piasek, E. J.; Mark, L. H. J. Org. Chem. 1961, 26, 2659.
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Filler, R.1
Piasek, E.J.2
Mark, L.H.3
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0024432538
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Takano, S.; Iwabuchi, Y.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1989, 1371.
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Takano, S.1
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36
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27644538717
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note
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-4.
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-
-
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37
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0034763234
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Similar observation in 3,4,6-triphenylpyrone system: (a) Hirano, K.; Minakata, S.; Komatsu, M. Bull. Chem. Soc. Jpn. 2001, 74, 1567.
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Hirano, K.1
Minakata, S.2
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0037118387
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(b) Hirano, K.; Minakata, S.; Komatsu, M.; Mizuguchi, J. J. Phys. Chem. A 2002, 106, 4868.
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Hirano, K.1
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Komatsu, M.3
Mizuguchi, J.4
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39
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27644443546
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note
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A reviewer kindly suggested an alternative possibility for the lack of fluorescence of compound 3af: efficient energy transfer to the fluorenyl moiety followed by nonradiative decay of the excited state. Thus, further studies are required to establish the detail of the structural effect.
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