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84958690531
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267-335 The Nef isocyanide reaction stands for the formation of imidoyl halides from acyl halides and isocyanides. If one considers the following additions of nucleophilic reagents to form stable adducts such as pyruvamides after water addition, it represents the first (sequential) three-component coupling of isocyanides. For references
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The Nef isocyanide reaction stands for the formation of imidoyl halides from acyl halides and isocyanides. If one considers the following additions of nucleophilic reagents to form stable adducts such as pyruvamides after water addition, it represents the first (sequential) three-component coupling of isocyanides. For references, see: Nef, J. U. Justus Liebigs Ann. Chem. 1892, 270, 267-335
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For a review on dihalogenoisocyanides
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For a review on dihalogenoisocyanides see: Kühle, E.; Anders, B.; Klauke, E.; Tarnow, H.; Zumach, G. Angew. Chem., Int. Ed. 1969, 8, 20-34
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An isocyanide dihalogenide conversion to chloropyridines followed by a palladium coupling has been reported in a synthesis of variolin analogues. However, with the low yields obtained in the first step, a one-pot multicomponent strategy may be very difficult to settle:;;;,-2601 For an additional cascade involving the cyclization of an isocyanide followed by a Suzuki coupling see:;;;;; Tetrahedron Lett. 2009, 50, 6715-6719
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An isocyanide dihalogenide conversion to chloropyridines followed by a palladium coupling has been reported in a synthesis of variolin analogues. However, with the low yields obtained in the first step, a one-pot multicomponent strategy may be very difficult to settle: Baeza, A.; Burgos, C.; Alvarez-Builla, J.; Vaquero, J. J. Tetrahedron Lett. 2007, 48, 2597-2601 For an additional cascade involving the cyclization of an isocyanide followed by a Suzuki coupling see: Liu, L.; Wang, Y.; Wang, H.; Peng, C.; Zhao, J.; Zhu, Q. Tetrahedron Lett. 2009, 50, 6715-6719
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79952179966
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For reduction of isocyanide dichloride under pallado-catalyzed Grignard addition
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For reduction of isocyanide dichloride under pallado-catalyzed Grignard addition see: Ito, Y.; Inouye, M.; Murakami, M. Tetrahedron. Lett. 1988, 29, 181-192
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79952175364
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For tetrazole formation from isocyanide dichlorides
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3, see:;; J. Am. Chem. Soc. 1967, 89, 2077-2082
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3, see: Fowler, F. W.; Hassner, A.; Levy, L. A. J. Am. Chem. Soc. 1967, 89, 2077-2082
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79952119823
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Without such a cyclization, sequential nucleophilic additions lead to imines prone to hydrolytic cleavage unless engaged in further reactions.
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Without such a cyclization, sequential nucleophilic additions lead to imines prone to hydrolytic cleavage unless engaged in further reactions.
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0001060231
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Due to the high complexing properties of isocyanides towards transition metals, catalyzed processes are difficult to settle unless using sterically hindered isocyanides:;,-239 For some representative examples see:;; Angew. Chem., Int. Ed. 2000, 39, 4156-4158
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Due to the high complexing properties of isocyanides towards transition metals, catalyzed processes are difficult to settle unless using sterically hindered isocyanides: Yamamoto, Y.; Yamazaki, H. Coord. Chem. Rev. 1972, 8, 225-239 For some representative examples see: Saluste, C. G.; Whitby, R. J.; Furber, M. Angew. Chem., Int. Ed. 2000, 39, 4156-4158
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