Convenient synthesis of alkylhydrazides by the cobalt-catalyzed hydrohydrazination reaction of olefins and azodicarboxylates
2004
Résumé
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)]
Détails
Titre
Convenient synthesis of alkylhydrazides by the cobalt-catalyzed hydrohydrazination reaction of olefins and azodicarboxylates
Auteur(s)
Waser, Jerome ; Carreira, Erick M.
Publié dans
Journal of the American Chemical Society
Volume
126
Numéro
18
Pages
5676-5677
Date
2004
ISSN
0002-7863
Mots-clés (libres)
Amination (reductive; stereoselective hydrohydrazination; regio- and stereoselective prepn. of alkylhydrazides via cobalt-catalyzed stereoselective hydrohydrazination of olefins with di-tert-Bu azodicarboxylate); Asymmetric synthesis and induction (regio- and stereoselective prepn. of alkylhydrazides via cobalt-catalyzed stereoselective hydrohydrazination of olefins with di-tert-Bu azodicarboxylate); Alkenes Role: RCT (Reactant); RACT (Reactant or reagent) (regioselective prepn. of alkylhydrazides via cobalt-catalyzed hydrohydrazination of olefins with azodicarboxylates); olefin azodicarboxylate hydrohydrazination; alkylhydrazide prepn; cobalt hydrohydrazination catalyst
Note
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)
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)
Laboratoires
LCSO
Le document apparaît dans
Production scientifique et compétences > SB - Faculté des sciences de base > ISIC - Institut des sciences et ingénierie chimiques > LCSO - Laboratoire de catalyse et synthèse organique
Publications validées par des pairs
Travail hors EPFL
Articles de journaux
Publié
Publications validées par des pairs
Travail hors EPFL
Articles de journaux
Publié
Date de création de la notice
2007-12-17