Cobalt-Catalyzed Hydroazidation of Olefins: Convenient Access to Alkyl Azides
Conversion of unactivated olefins to azides was achieved with high Markovnikov selectivity for a broad range of alkenes by using 6 mol % Co(BF4).6H2O and ligand I, with 3 equiv of tosyl azide as the nitrogen source and simple silanes (e.g., PhSiH3, tetramethyldisiloxane). [on SciFinder (R)]
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Waser, J., Nambu, H., & Carreira, E. M. (2005). Cobalt-Catalyzed Hydroazidation of Olefins: Convenient Access to Alkyl Azides. Journal of the American Chemical Society, 127(23), 8294–8295. https://doi.org/10.1021/ja052164r
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2005
127
23
8294
8295
CAN 143:133069
23-5
Aliphatic Compounds
Laboratorium fuer Organische Chemie,ETH Hoenggerberg,Zurich,Switz.
Journal
written in English.
15684-35-2 (Cobalt bis(tetrafluoroborate) hexahydrate); 15684-35-2D (Cobalt bis(tetrafluoroborate) hexahydrate); 858344-69-1D Role: CAT (Catalyst use), USES (Uses) (prepn. of alkyl azides via cobalt-catalyzed hydroazidation of olefins); 858344-69-1P Role: CAT (Catalyst use), RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), USES (Uses), RACT (Reactant or reagent) (prepn. of alkyl azides via cobalt-catalyzed hydroazidation of olefins); 6147-53-1; 10026-22-9 (Cobalt dinitrate hexahydrate) Role: CAT (Catalyst use), RGT (Reagent), USES (Uses), RACT (Reactant or reagent) (prepn. of alkyl azides via cobalt-catalyzed hydroazidation of olefins); 704900-51-6P; 858671-40-6P; 858671-46-2P Role: CAT (Catalyst use), SPN (Synthetic preparation), PREP (Preparation), USES (Uses) (prepn. of alkyl azides via cobalt-catalyzed hydroazidation of olefins); 62-57-7 (2-Aminoisobutyric acid); 90-02-8 (Salicylaldehyde); 94-59-7; 98-86-2 (Acetophenone); 100-39-0 (Benzyl bromide); 106-95-6 (Allyl bromide); 107-18-6 (Allyl alcohol); 127-91-3; 513-42-8 (Methallyl alcohol); 536-74-3 (Phenylacetylene); 556-82-1 (3-Methyl-2-butenol); 563-47-3 (Methallyl chloride); 591-80-0 (4-Pentenoic acid); 627-27-0 (3-Buten-1-ol); 768-56-9; 939-26-4 (2-(Bromomethyl)naphthalene); 941-55-9 (Tosyl azide); 1730-25-2 (Allylmagnesium bromide); 3060-50-2 (alpha,alpha-Diphenylglycine); 14593-43-2; 37942-07-7 (3,5-Di-tert-butylsalicylaldehyde); 58479-61-1 (tert-Butyldiphenylsilyl chloride); 75031-69-5 (Butoxy-tert-butyldiphenylsilane); 221313-63-9 (Propoxy-tert-butyldiphenylsilane); 858344-71-5 (3-(Diphenylphosphinoyl)-3-methyl-5-phenylpentan-2-ol) Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of alkyl azides via cobalt-catalyzed hydroazidation of olefins); 2489-89-6P; 3240-29-7P; 6683-51-8P; 72485-49-5P; 105966-43-6P; 113882-48-7P; 135006-32-5P; 136787-49-0P; 188263-82-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of alkyl azides via cobalt-catalyzed hydroazidation of olefins); 694-53-1 (Phenylsilane); 30110-74-8 (Tetramethyldisiloxane) Role: RGT (Reagent), RACT (Reactant or reagent) (prepn. of alkyl azides via cobalt-catalyzed hydroazidation of olefins); 104-51-8P (1-Phenylbutane); 22374-89-6P; 32366-28-2P; 58977-25-6P; 166327-12-4P; 475152-60-4P; 858344-60-2P; 858344-61-3P; 858344-62-4P; 858344-63-5P; 858344-64-6P; 858344-65-7P; 858344-66-8P; 858344-67-9P; 858344-68-0P; 858344-70-4P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of alkyl azides via cobalt-catalyzed hydroazidation of olefins)
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