Palladium-Catalyzed Branch-Selective Allylic C–H Amination Enabled by Nucleophile Coordination

Regiochemical control is a central subject in the field of synthetic chemistry. Here we unveil an innovative approach for the branch-selective allylic C–H amination of α-alkenes with amine nucleophiles facilitated by phosphoramidite–palladium catalysis. A diverse array of α-alkenes has been effectiv...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 26; no. 40; pp. 8481 - 8485
Main Authors Nong, Zhong-Sheng, Wang, Pu-Sheng, Zhou, Qi-Lin, Gong, Liu-Zhu
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 11.10.2024
Amer Chemical Soc
Subjects
amination
catalytic activity
Chemistry
Chemistry, Organic
enantioselectivity
Lewis bases
ligands
Physical Sciences
regioselectivity
Science & Technology
SUBSTITUTION
ACETYLENES
ASYMMETRIC-SYNTHESIS
KINETIC RESOLUTION
HOMOBENZOTETRAMISOLE
ALLYLATION
DIAMINATION
OLEFINS
TERMINAL ALKENES
STRATEGIES
Online AccessGet full text

Cover

More Information
Summary:Regiochemical control is a central subject in the field of synthetic chemistry. Here we unveil an innovative approach for the branch-selective allylic C–H amination of α-alkenes with amine nucleophiles facilitated by phosphoramidite–palladium catalysis. A diverse array of α-alkenes has been effectively utilized to produce a variety of structurally distinct allylamines with moderate to excellent regioselectivity. Furthermore, the asymmetric version of this reaction is feasible through the use of chiral phosphoramidite ligands, albeit with currently modest enantioselectivity.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c02935