Catalyst‐free Decarboxylation and Decarboxylative Giese Additions of Alkyl Carboxylates through Photoactivation of Electron Donor‐Acceptor Complex

We report herein a catalyst‐free method to perform decarboxylative conjugated addition and hydrodecarboxylation of aliphatic N‐(acyloxy)phthalimides (redox active esters, RAEs) through photoactivation of electron‐donor‐acceptor (EDA) complex with Hantzsch ester (HE) in N,N‐dimethylacetamide (DMA) so...

Full description

Saved in:
Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 361; no. 19; pp. 4500 - 4505
Main Authors Zheng, Chao, Wang, Guang‐Zu, Shang, Rui
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 08.10.2019
Wiley Subscription Services, Inc
Subjects
Aliphatic compounds
Carbon
Carboxylates
Catalysts
Chemistry
Chemistry, Applied
Chemistry, Organic
Coordination compounds
Decarboxylation
EDA complex
Esters
Functional groups
Giese Additions
Light irradiation
Photoactivation
Phthalimides
Physical Sciences
Redox Active Ester
Science & Technology
Substrates
EDA complex
Photoactivation
ACIDS
LIGHT
Redox Active Ester
QUATERNARY CARBONS
TERTIARY
RADICAL DECARBOXYLATION
PHOTOREDOX CATALYSIS
Giese Additions
Decarboxylation
GENERATION
REDOX-ACTIVE ESTERS
HECK REACTION
N-(ACYLOXY)PHTHALIMIDES
Online AccessGet full text

Cover

More Information
Summary:We report herein a catalyst‐free method to perform decarboxylative conjugated addition and hydrodecarboxylation of aliphatic N‐(acyloxy)phthalimides (redox active esters, RAEs) through photoactivation of electron‐donor‐acceptor (EDA) complex with Hantzsch ester (HE) in N,N‐dimethylacetamide (DMA) solution. The reactions present a green method to decarboxylatively construct carbon‐carbon bond and to perform hydrodecarboxylation with broad substrate scope and functional group tolerance under mild blue light irradiation condition without recourse of popularly used photoredox catalysts.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201900803