Direct Access to Primary Amines from Alkenes by Selective Metal‐Free Hydroamination

Direct and selective synthesis of primary amines from easily available precursors is attractive yet challenging. Herein, we report the rapid synthesis of primary amines from alkenes via metal‐free regioselective hydroamination at room temperature. Ammonium carbonate was used as ammonia surrogate for...

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Bibliographic Details
Published in:Angewandte Chemie International Edition Vol. 60; no. 18; pp. 9875 - 9880
Main Authors: Du, Yi‐Dan, Chen, Bi‐Hong, Shu, Wei
Format: Journal Article
Language:English
Published: WEINHEIM Wiley 26.04.2021
Wiley Subscription Services, Inc
Edition:International ed. in English
Subjects:
alkene
Alkenes
Amines
Ammonia
Ammonium
ammonium carbonate
Ammonium compounds
Chemistry
Chemistry, Multidisciplinary
hydroamination
metal-free
Physical Sciences
primary amines
Room temperature
Science & Technology
Synthesis
primary amines
ACIDS
ANTI-MARKOVNIKOV HYDROAMINATION
ALKYLAMINES
metal-free
CATALYZED HYDROAMINATION
hydroamination
PHOTOREDOX CATALYSIS
HYDRIDE
ALCOHOLS
AMINATION
alkene
OLEFINS
ammonium carbonate
ISSN:1433-7851, 1521-3773, 1521-3773
Online Access:Get full text
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Summary:Direct and selective synthesis of primary amines from easily available precursors is attractive yet challenging. Herein, we report the rapid synthesis of primary amines from alkenes via metal‐free regioselective hydroamination at room temperature. Ammonium carbonate was used as ammonia surrogate for the first time, allowing for efficient conversion of terminal and internal alkenes into linear, α‐branched, and α‐tertiary primary amines under mild conditions. This method provides a straightforward and powerful approach to a wide spectrum of advanced, highly functionalized primary amines which are of particular interest in pharmaceutical chemistry and other areas. A straightforward and modular route to a wide variety of aliphatic primary amines from alkenes is presented based on a metal‐free hydroamination at room temperature. The use of cost‐effective and easily available ammonium carbonate allows for the efficient conversion of terminal and internal alkenes with diverse substitution patterns into highly functionalized linear, α‐branched, and α‐tertiary primary amines.
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ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.202016679