Iron-Catalyzed Allylic Amination Directly from Allylic Alcohols

Balakumar Emayavaramban; Moumita Roy; Basker Sundararaju

doi:10.1002/chem.201505214

Iron-Catalyzed Allylic Amination Directly from Allylic Alcohols

Chemistry. 2016 Mar 14;22(12):3952-5. doi: 10.1002/chem.201505214. Epub 2016 Feb 17.

Authors

Balakumar Emayavaramban¹, Moumita Roy¹, Basker Sundararaju²

Affiliations

¹ Fine Chemical Laboratory, Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, Uttar Pradesh, India.
² Fine Chemical Laboratory, Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, Uttar Pradesh, India. basker@iitk.ac.in.

PMID: 26812622
DOI: 10.1002/chem.201505214

Abstract

Allylic amination, directly from alcohols, has been demonstrated without any Lewis acid activators using an efficient and regiospecific molecular iron catalyst. Various amines and alcohols were employed and the reaction proceeded through the oxidation/reduction (redox) pathway. A direct one-step synthesis of common drugs, such as cinnarizine and nafetifine, was exhibited from cinnamyl alcohol that produced water as side product.

Keywords: alcohols; allylic compounds; amination; hydrogen borrowing; iron.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Allyl Compounds / chemical synthesis
Amination
Amines / chemical synthesis
Catalysis
Iron / chemistry*
Oxidation-Reduction
Propanols / chemistry*

Substances

Allyl Compounds
Amines
Propanols
allyl alcohol
Iron
cinnamyl alcohol