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4043179055
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Ni complexes readily undergo oxidative addition of both alkyl- and aryl- CN bonds. For example, Ni complexes catalyze the carbocyanation of alkynes: (a) García, J. J.; Arévalo, A.; Brunkan, N. M.; Jones, W. D. Organometallics 2004, 23, 3997.
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28
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17144398186
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note
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Ni complexes are known to cause homodimerization of nitriles (see ref 9).
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29
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17144430616
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note
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Both SIPr and IPr ligands readily dissociate from Ni(0). even upon the addition of COD (see ref 10a).
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30
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17144403953
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note
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Unsaturated analogue IPr gave slightly lower conversion under identical reaction conditions (99% versus 66% for SIPr and IPr, respectively) (IPr = 1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene; SIPr = 1,3-bis-(2,6- diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene).
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31
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17144375422
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note
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This is in contrast to the Ni/NHC-catalyzed route to pyridones where electron-deficient isocyanates required elevated temperatures for complete cycloaddition (see ref 11).
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32
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7444240351
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(a) Siriwardana, A. I.; Kathriarachchi, K. K. A. D. S.; Nakamura, I.; Gridnev, I. D.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 13898.
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Yamamoto, Y.5
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33
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11144246890
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(b) Sarkar, T. K.; Basak, S.; Wainer, I.; Moaddel, R.; Yamaguchi, R.; Jozwiak, K.; Chen, H.-T.; Lin, C.-C. J. Med. Chem. 2004, 47, 6691.
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Sarkar, T.K.1
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Chen, H.-T.7
Lin, C.-C.8
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34
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17144401250
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note
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Cycloaddition with acetonitrile (2e) afforded 2,3,4,5-tetraethyl-6- methylpyridine (25) in 25% yield. See Supporting Information.
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