research article

Cobalt-Catalyzed Hydrohydrazination of Dienes and Enynes: Access to Allylic and Propargylic Hydrazides

Waser, Jerome  
•
Gonzalez-Gomez, Jose C.
•
Nambu, Hisanori
Show more
2005
Organic Letters

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)]

Type
research article
DOI
10.1021/ol0517473
Author(s)
Waser, Jerome  
•
Gonzalez-Gomez, Jose C.
•
Nambu, Hisanori
•
Huber, Pascal
•
Carreira, Erick M.
Date Issued

2005

Published in
Organic Letters
Volume

7

Issue

19

Start page

4249

End page

4252

Subjects

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)

Editorial or Peer reviewed

REVIEWED

Written at

OTHER

EPFL units
LCSO  
Available on Infoscience
December 17, 2007
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/15790