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1H NMR. The Z configuration of the exocyclic double bond of 3aa was assigned by an NOE study.
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1H NMR. The Z configuration of the exocyclic double bond of 3aa was assigned by an NOE study.
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For a Pd(II)-catalyzed addition reaction of arylboronic acids, see; (a) Nishikata, T.; Yamamoto, Y.; Miyaura, N. Angew. Chem., Int. Ed. 2003, 42, 2768.
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For a Pd(II)-catalyzed addition reaction of arylboronic acids, see; (a) Nishikata, T.; Yamamoto, Y.; Miyaura, N. Angew. Chem., Int. Ed. 2003, 42, 2768.
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For a Pd(II)-catalyzed cyclization reaction of alkynones with arylboronic acids, see: (a) Song, J.; Shen, Q.; Xu, F.; Lu, X. Org. Lett. 2007, 9, 2947.
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At this time, it is not possible to rale out a mechanism involving sequential carbopalladation steps, initially operating on the alkyne moiety and next on the isocyanate moiety in a stepwise manner. For oxidative addition of arylboronic acids to Pd(O), see: (a) Cho, C. S.; Uemura, S. J. Organomet. Chem. 1994, 465, 85.
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For a Pd(0)-catalyzed alkynylation reaction of aryl halides with alkynylboronates or alkynylborates, see: (a) Castanet, A.-S.; Colobert, F.; Schlama, T. Org. Lett. 2000, 2, 3559.
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For a review of P(2-furyl)3 as ligand, see: (b) Andersen, N. G.; Keay, B. A. Chem. Rev. 2001, 101, 997.
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37
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60949085520
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4 was less effective, and its use under the same reaction conditions gave 3a1 in 42% yield (Z/E = 56/44).
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4 was less effective, and its use under the same reaction conditions gave 3a1 in 42% yield (Z/E = 56/44).
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38
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60949095409
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As reported in ref 4a, the E/Z isomerization of alkynylated 3-alkylideneoxindoles was caused by the phosphine ligand. (17) Alkynylboronate 2m was so labile that it was handled in a glovebox.
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As reported in ref 4a, the E/Z isomerization of alkynylated 3-alkylideneoxindoles was caused by the phosphine ligand. (17) Alkynylboronate 2m was so labile that it was handled in a glovebox.
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