Cobalt-Catalyzed Hydrohydrazination of Dienes and Enynes: Access to Allylic and Propargylic Hydrazides
2005
Abstract
The cobalt-catalyzed hydrohydrazination reaction of dienes and enynes is presented. Allylic and propargylic hydrazides were obtained in synthetically useful yields (allylic amines, 60-90%; propargylic amines, 47-83%) and good chemo- and regioselectivity. [on SciFinder (R)]
Details
Title
Cobalt-Catalyzed Hydrohydrazination of Dienes and Enynes: Access to Allylic and Propargylic Hydrazides
Author(s)
Waser, Jerome ; Gonzalez-Gomez, Jose C. ; Nambu, Hisanori ; Huber, Pascal ; Carreira, Erick M.
Published in
Organic Letters
Volume
7
Issue
19
Pages
4249-4252
Date
2005
ISSN
1523-7060
Keywords
Addition reaction; Addition reaction catalysts (prepn. of allylic and propargylic hydrazides by cobalt-catalyzed hydrohydrazination of dienes and enynes); Alkadienes; Alkenynes Role: RCT (Reactant); RACT (Reactant or reagent) (prepn. of allylic and propargylic hydrazides by cobalt-catalyzed hydrohydrazination of dienes and enynes); Hydrazides Role: SPN (Synthetic preparation); PREP (Preparation) (unsatd.; prepn. of allylic and propargylic hydrazides by cobalt-catalyzed hydrohydrazination of dienes and enynes); hydrazide allyl propargyl prepn hydrohydrazination alkadiene alkenyne
Note
CAN 143:366972
23-5
Aliphatic Compounds
Laboratorium fuer Organische Chemie,ETH Hoenggerberg,Zurich,Switz.
Journal
written in English.
866487-21-0P Role: CAT (Catalyst use), SPN (Synthetic preparation), PREP (Preparation), USES (Uses) (prepn. of allylic and propargylic hydrazides by cobalt-catalyzed hydrohydrazination of dienes and enynes); 62-57-7 (2-Aminoisobutyric acid); 71-48-7 (Cobalt(II) acetate); 78-79-5 (Isoprene); 78-80-8 (2-Methylbut-1-en-3-yne); 90-02-8 (Salicylaldehyde); 100-07-2 (Anisoyl chloride); 115-19-5 (2-Methyl-3-butyn-2-ol); 123-35-3 (Myrcene); 513-81-5 (2,3-Dimethyl-1,3-butadiene); 536-74-3 (Phenylacetylene); 542-92-7 (Cyclopentadiene); 590-14-7 (1-Bromo-1-propene); 592-57-4 (1,3-Cyclohexadiene); 593-60-2 (Vinyl bromide); 693-02-7 (1-Hexyne); 764-13-6 (2,5-Dimethyl-2,4-hexadiene); 870-50-8 (Di-tert.-butyl azodicarboxylate); 922-67-8 (Methyl propiolate); 1066-54-2 (Trimethylsilylacetylene); 1700-10-3 (1,3-Cyclooctadiene); 1972-28-7 (Diethyl azodicarboxylate); 4054-38-0 (1,3-Cycloheptadiene); 4341-76-8 (Ethyl 2-butynoate); 10141-05-6 (Cobalt(II) nitrate); 158389-19-6; 161374-36-3 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of allylic and propargylic hydrazides by cobalt-catalyzed hydrohydrazination of dienes and enynes); 690-94-8P; 2696-32-4P; 13633-26-6P; 17679-92-4P (1-Octen-3-yne); 18387-60-5P; 18387-62-7P; 56053-90-8P; 62000-92-4P; 121635-27-6P; 211060-30-9P; 866487-22-1P; 866487-23-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of allylic and propargylic hydrazides by cobalt-catalyzed hydrohydrazination of dienes and enynes); 39203-22-0P; 226892-01-9P; 866487-24-3P; 866487-25-4P; 866487-26-5P; 866487-27-6P; 866487-28-7P; 866487-29-8P; 866487-30-1P; 866487-31-2P; 866487-33-4P; 866487-34-5P; 866487-35-6P; 866487-36-7P; 866487-37-8P; 866487-38-9P; 866487-39-0P; 866487-40-3P; 866487-41-4P; 866487-42-5P; 866487-44-7P; 866487-45-8P; 866487-46-9P; 866487-47-0P; 866487-48-1P; 866487-49-2P; 866487-50-5P; 866487-51-6P; 866487-52-7P; 866487-53-8P; 866487-54-9P; 866487-55-0P; 866487-56-1P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of allylic and propargylic hydrazides by cobalt-catalyzed hydrohydrazination of dienes and enynes)
23-5
Aliphatic Compounds
Laboratorium fuer Organische Chemie,ETH Hoenggerberg,Zurich,Switz.
Journal
written in English.
866487-21-0P Role: CAT (Catalyst use), SPN (Synthetic preparation), PREP (Preparation), USES (Uses) (prepn. of allylic and propargylic hydrazides by cobalt-catalyzed hydrohydrazination of dienes and enynes); 62-57-7 (2-Aminoisobutyric acid); 71-48-7 (Cobalt(II) acetate); 78-79-5 (Isoprene); 78-80-8 (2-Methylbut-1-en-3-yne); 90-02-8 (Salicylaldehyde); 100-07-2 (Anisoyl chloride); 115-19-5 (2-Methyl-3-butyn-2-ol); 123-35-3 (Myrcene); 513-81-5 (2,3-Dimethyl-1,3-butadiene); 536-74-3 (Phenylacetylene); 542-92-7 (Cyclopentadiene); 590-14-7 (1-Bromo-1-propene); 592-57-4 (1,3-Cyclohexadiene); 593-60-2 (Vinyl bromide); 693-02-7 (1-Hexyne); 764-13-6 (2,5-Dimethyl-2,4-hexadiene); 870-50-8 (Di-tert.-butyl azodicarboxylate); 922-67-8 (Methyl propiolate); 1066-54-2 (Trimethylsilylacetylene); 1700-10-3 (1,3-Cyclooctadiene); 1972-28-7 (Diethyl azodicarboxylate); 4054-38-0 (1,3-Cycloheptadiene); 4341-76-8 (Ethyl 2-butynoate); 10141-05-6 (Cobalt(II) nitrate); 158389-19-6; 161374-36-3 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of allylic and propargylic hydrazides by cobalt-catalyzed hydrohydrazination of dienes and enynes); 690-94-8P; 2696-32-4P; 13633-26-6P; 17679-92-4P (1-Octen-3-yne); 18387-60-5P; 18387-62-7P; 56053-90-8P; 62000-92-4P; 121635-27-6P; 211060-30-9P; 866487-22-1P; 866487-23-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of allylic and propargylic hydrazides by cobalt-catalyzed hydrohydrazination of dienes and enynes); 39203-22-0P; 226892-01-9P; 866487-24-3P; 866487-25-4P; 866487-26-5P; 866487-27-6P; 866487-28-7P; 866487-29-8P; 866487-30-1P; 866487-31-2P; 866487-33-4P; 866487-34-5P; 866487-35-6P; 866487-36-7P; 866487-37-8P; 866487-38-9P; 866487-39-0P; 866487-40-3P; 866487-41-4P; 866487-42-5P; 866487-44-7P; 866487-45-8P; 866487-46-9P; 866487-47-0P; 866487-48-1P; 866487-49-2P; 866487-50-5P; 866487-51-6P; 866487-52-7P; 866487-53-8P; 866487-54-9P; 866487-55-0P; 866487-56-1P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of allylic and propargylic hydrazides by cobalt-catalyzed hydrohydrazination of dienes and enynes)
Laboratories
LCSO
Record Appears in
Scientific production and competences > SB - School of Basic Sciences > ISIC - Institute of Chemical Sciences and Engineering > LCSO - Laboratory of Catalysis and Organic Synthesis
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published
Record creation date
2007-12-17