Convenient synthesis of alkylhydrazides by the cobalt-catalyzed hydrohydrazination reaction of olefins and azodicarboxylates
Treatment of olefins with an excess of di-tert-Bu azodicarboxylate, an equimolar amt. of PhSiH3, and a catalytic amt. of a Co(III) catalyst afforded the Markovnikov hydrazide products, e.g., I, for a broad range of olefins, in good yields. [on SciFinder (R)]
2004
126
18
5676
5677
CAN 141:38374
24-7
Alicyclic Compounds
Laboratorium fuer Organische Chemie,ETH Hoenggerberg,Zurich,Switz.
Journal
written in English.
62-57-7 (2-Aminoisobutyric acid); 90-02-8 (Salicylaldehyde) Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. and catalyst use of sodium bis[N-salicylidene(amino)isobutyrato]cobaltate via condensation of salicylaldehyde with aminoisobutyric acid followed by complexation with cobalt nitrate); 110-83-8 (Cyclohexene); 142-29-0 (Cyclopentene); 498-66-8 (Norbornene); 931-88-4 (Cyclooctene) Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of alkylhydrazides via cobalt-catalyzed hydrohydrazination of olefins with di-tert-Bu azodicarboxylate); 180137-93-3P; 345210-67-5P; 704900-46-9P; 704900-48-1P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of alkylhydrazides via cobalt-catalyzed hydrohydrazination of olefins with di-tert-Bu azodicarboxylate); 5794-03-6; 18172-67-3 Role: RCT (Reactant), RACT (Reactant or reagent) (regio- and stereoselective prepn. of alkylhydrazides via cobalt-catalyzed stereoselective hydrohydrazination of olefins with di-tert-Bu azodicarboxylate); 704900-32-3P; 704900-36-7P Role: SPN (Synthetic preparation), PREP (Preparation) (regio- and stereoselective prepn. of alkylhydrazides via cobalt-catalyzed stereoselective hydrohydrazination of olefins with di-tert-Bu azodicarboxylate); 704900-51-6P Role: CAT (Catalyst use), SPN (Synthetic preparation), PREP (Preparation), USES (Uses) (regioselective prepn. of alkylhydrazides via cobalt-catalyzed hydrohydrazination of olefins with azodicarboxylates); 95-13-6 (Indene); 98-83-9 (alpha-Methylstyrene); 100-42-5 (Styrene); 104-54-1 (3-Phenyl-2-propen-1-ol); 107-18-6 (Allyl alcohol); 109-49-9 (5-Hexen-2-one); 556-82-1 (3-Methyl-2-buten-1-ol); 598-32-3 (3-Buten-2-ol); 637-50-3; 763-29-1 (2-Methyl-1-pentene); 768-56-9 (4-Phenyl-1-butene); 771-98-2 (1-Phenyl-1-cyclohexene); 870-50-8 (Di-tert-butyl azodicarboxylate); 1192-37-6 (Methylenecyclohexane); 1972-28-7 (Diethyl azodicarboxylate); 5162-44-7 (4-Bromo-1-butene); 6044-68-4 (Acrolein dimethyl acetal); 6117-91-5 (Crotyl alcohol); 10544-63-5 (Ethyl 2-butenoate); 14593-43-2 (Allyl benzyl ether) Role: RCT (Reactant), RACT (Reactant or reagent) (regioselective prepn. of alkylhydrazides via cobalt-catalyzed hydrohydrazination of olefins with azodicarboxylates); 126745-48-0P; 704899-84-3P; 704899-87-6P; 704899-91-2P; 704899-94-5P; 704899-98-9P; 704900-03-8P; 704900-06-1P; 704900-09-4P; 704900-12-9P; 704900-15-2P; 704900-18-5P; 704900-21-0P; 704900-24-3P; 704900-28-7P; 704900-40-3P; 704900-42-5P; 704900-44-7P; 704900-53-8P; 704900-57-2P Role: SPN (Synthetic preparation), PREP (Preparation) (regioselective prepn. of alkylhydrazides via cobalt-catalyzed hydrohydrazination of olefins with azodicarboxylates)
REVIEWED