Asymmetric Markovnikov Hydroaminocarbonylation of Alkenes Enabled by Palladium-Monodentate Phosphoramidite Catalysis

A palladium-catalyzed asymmetric Markovnikov hydroaminocarbonylation of alkenes with anilines has been developed for the atom-economical synthesis of 2-substituted propanamides bearing an alpha-stereocenter. A novel phosphoramidite ligand L16 was discovered which exhibited very high reactivity and s...

Full description

Saved in:
Bibliographic Details
Published inJournal of the American Chemical Society Vol. 143; no. 1; pp. 85 - 91
Main Authors Yao, Ya-Hong, Yang, Hui-Yi, Chen, Ming, Wu, Fei, Xu, Xing-Xing, Guan, Zheng-Hui
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 13.01.2021
Subjects
alkenes
catalytic activity
Chemistry
Chemistry, Multidisciplinary
enantioselective synthesis
hydrides
ligands
palladium
Physical Sciences
Science & Technology
ALKOXYCARBONYLATION
CARBONYLATION
CARBON-MONOXIDE
METHYL PROPANOATE
REGIOSELECTIVE SYNTHESIS
OLEFINS
AMINOCARBONYLATION
METHOXYCARBONYLATION
HYDROXYCARBONYLATION
HYDROESTERIFICATION
Online AccessGet full text

Cover

More Information
Summary:A palladium-catalyzed asymmetric Markovnikov hydroaminocarbonylation of alkenes with anilines has been developed for the atom-economical synthesis of 2-substituted propanamides bearing an alpha-stereocenter. A novel phosphoramidite ligand L16 was discovered which exhibited very high reactivity and selectivity in the reaction. This asymmetric Markovnikov hydroaminocarbonylation employs readily available starting materials and tolerates a wide range of functional groups, thus providing a facile and straightforward method for the regio- and enantioselective synthesis of 2-substituted propanamides under ambient conditions. Mechanistic studies revealed that the reaction proceeds through a palladium hydride pathway.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.0c11249