English
 
Help Privacy Policy Disclaimer
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT
  Efficient access to unprotected primary amines by iron-catalyzed aminochlorination of alkenes

Legnani, L., Prina Cerai, G., Delcaillau, T., Willems, S., & Morandi, B. (2018). Efficient access to unprotected primary amines by iron-catalyzed aminochlorination of alkenes. Science, 362(6413), 434-438. doi:10.1126/science.aat3863.

Item is

Basic

show hide
Genre: Journal Article

Files

show Files

Locators

show

Creators

show
hide
 Creators:
Legnani, Luca1, Author              
Prina Cerai, Gabriele1, Author              
Delcaillau, Tristan1, 2, Author              
Willems, Suzanne1, Author              
Morandi, Bill1, 2, Author              
Affiliations:
1Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2040309              
2ETH Zürich, Zürich, Switzerland, ou_persistent22              

Content

show
hide
Free keywords: -
 Abstract: Primary amines are essential constituents of biologically active molecules and versatile intermediates in the synthesis of drugs and agrochemicals. However, their preparation from easily accessible alkenes remains challenging. Here, we report a general strategy to access primary amines from alkenes through an operationally simple iron-catalyzed aminochlorination reaction. A stable hydroxylamine derivative and benign sodium chloride act as the respective nitrogen and chlorine sources. The reaction proceeds at room temperature under air; tolerates a large scope of aliphatic and conjugated alkenes, including densely functionalized substrates; and provides excellent anti-Markovnikov regioselectivity with respect to the amino group. The reactivity of the 2-chloroalkylamine products, an understudied class of amphoteric molecules, enables facile access to linear or branched aliphatic amines, aziridines, aminonitriles, azido amines, and homoallylic amines.

Details

show
hide
Language(s): eng - English
 Dates: 2018-02-212018-09-042018-10-26
 Publication Status: Published in print
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1126/science.aat3863
 Degree: -

Event

show

Legal Case

show

Project information

show

Source 1

show
hide
Title: Science
  Other : Science
Source Genre: Journal
 Creator(s):
Affiliations:
Publ. Info: Washington, D.C. : American Association for the Advancement of Science
Pages: - Volume / Issue: 362 (6413) Sequence Number: - Start / End Page: 434 - 438 Identifier: ISSN: 0036-8075
CoNE: https://pure.mpg.de/cone/journals/resource/991042748276600_1