Ruthenium-catalyzed regioselective allylic amination of 2,3,3-trifluoroallylic carbonates

2017 ◽  
Vol 15 (14) ◽  
pp. 2938-2946 ◽  
Author(s):  
Shin-ichi Isobe ◽  
Shou Terasaki ◽  
Taisyun Hanakawa ◽  
Shota Mizuno ◽  
Motoi Kawatsura
Keyword(s):  
Allylic Amines ◽  
Allylic Amination ◽  
Terminal Alkenes

Synthesis of trifluorinated terminal alkenes possessing allylic amines by ruthenium-catalyzed branch selective allylic amination.

Practical regio- and stereoselective azidation and amination of terminal alkenes

2018 ◽  
Vol 16 (48) ◽  
pp. 9354-9358 ◽  
Author(s):  
Olatunji S. Ojo ◽  
Octavio Miranda ◽  
Kyle C. Baumgardner ◽  
Alejandro Bugarin
Keyword(s):  
Allylic Amines ◽  
Reaction Conditions ◽  
Metal Free ◽  
Terminal Alkenes ◽  
Allylic Azides

A metal-free synthesis of allylic azides and allylic amines was achieved under mild reaction conditions, which represents a milder alternative for azidation and amination reactions.

Regioselective Synthesis of Optically Active Trifluoromethyl Group Substituted Allylic Amines by Palladium-Catalyzed Allylic Amination

Synlett ◽  
2010 ◽  
Vol 2010 (19) ◽  
pp. 2887-2890 ◽  
Author(s):  
Motoi Kawatsura ◽  
Toshiyuki Itoh ◽  
Takuya Hirakawa ◽  
Kazunori Ikeda ◽  
Hiroshi Ogasa
Keyword(s):  
Optically Active ◽  
Regioselective Synthesis ◽  
Trifluoromethyl Group ◽  
Allylic Amines ◽  
Allylic Amination ◽  
Palladium Catalyzed

Regioselective synthesis of trifluoromethyl group substituted allylic amines via palladium-catalyzed allylic amination

2008 ◽  
Vol 49 (15) ◽  
pp. 2450-2453 ◽  
Author(s):  
Motoi Kawatsura ◽  
Takuya Hirakawa ◽  
Tomoko Tanaka ◽  
Daiji Ikeda ◽  
Shuichi Hayase ◽  
...  
Keyword(s):  
Regioselective Synthesis ◽  
Trifluoromethyl Group ◽  
Allylic Amines ◽  
Allylic Amination ◽  
Palladium Catalyzed

ChemInform Abstract: Regioselective Synthesis of Trifluoromethyl Group Containing Allylic Amines by Palladium-Catalyzed Allylic Amination and Sequential Isomerization.

ChemInform ◽  
2012 ◽  
Vol 43 (12) ◽  
pp. no-no
Author(s):  
Takuya Hirakawa ◽  
Kazunori Ikeda ◽  
Daiji Ikeda ◽  
Tomoko Tanaka ◽  
Hiroshi Ogasa ◽  
...  
Keyword(s):  
Regioselective Synthesis ◽  
Trifluoromethyl Group ◽  
Allylic Amines ◽  
Allylic Amination ◽  
Palladium Catalyzed

scholarly journals Site-Selective Allylic C-H Amination with Aliphatic Amines

2021 ◽  
Author(s):  
Shengchun Wang ◽  
Yiming Gao ◽  
Demin Ren ◽  
He Sun ◽  
Linbin Niu ◽  
...  
Keyword(s):  
Hydrogen Atom ◽  
Building Blocks ◽  
Hydrogen Atom Transfer ◽  
Allylic Amines ◽  
Allylic Amination ◽  
Alkyl Amines ◽  
Reaction Proceeds ◽  
Bond Options ◽  
A Site ◽  
Site Selective

Abstract The direct coupling of olefins and alkyl amines represents the most efficient and atom-economical approach to prepare aliphatic allylamines which are fundamental building blocks. However, the method that achieves this goal while exhibiting exquisite control over the site at which the amine is introduced remains elusive. Herein, we report that the combination of a photocatalyst and a cobaloxime enables site-selective allylic C–H amination of olefins with secondary alkyl amines to afford allylic amines, eliminating the need for oxidants. This reaction proceeds by a radical-based mechanism distinct from those of existing allylic amination reactions. It affords the product resulting from cleavage of the stronger, primary allylic C–H bonds over other weaker allylic C–H bond options. DFT calculations reveal that this selectivity originates from a cobaloxime-promoted hydrogen atom transfer (HAT) process. Our method is compatible with a broad scope of alkenes, and can be extended to achieve a site- and diastereoselective amination of natural terpenes.

Sign in / Sign up

Export Citation Format

Share Document