Synthesis of stilbene derivatives via visible-light-induced cross-coupling of aryl diazonium salts with nitroalkenes using -NO2 as a leaving group

The straightforward visible-light-induced synthesis of stilbene compounds via the cross-coupling of nitroalkenes and diazonium tetra-fluoroborates under transition-metal-free conditions is described. The protocol uses green LEDs as light sources and eosin Y as an organophotoredox catalyst. Broad sub...

Full description

Saved in:
Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 52; no. 99; pp. 14234 - 14237
Main Authors Zhang, Na, Quan, Zheng-Jun, Zhang, Zhang, Da, Yu-Xia, Wang, Xi-Cun
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2016
Subjects
Aromatic compounds
Chemistry
Chemistry, Multidisciplinary
Cross coupling
Derivatives
Light sources
Light-emitting diodes
Physical Sciences
Radicals
Science & Technology
Stilbene
Synthesis
ORGANIC-SYNTHESIS
ALKENES
RESVERATROL
ACTIVATION
HECK-TYPE REACTION
ARYLATION
OLEFINS
CARBON-CARBON BONDS
ALKYNES
METAL-FREE
Online AccessGet full text

Cover

More Information
Summary:The straightforward visible-light-induced synthesis of stilbene compounds via the cross-coupling of nitroalkenes and diazonium tetra-fluoroborates under transition-metal-free conditions is described. The protocol uses green LEDs as light sources and eosin Y as an organophotoredox catalyst. Broad substrate scope and exclusive selectivity for the (E)-configuration of stilbenes are observed. This protocol proceeds via a radical pathway, with nitroalkenes serving as the radical acceptor, and the nitro group is cleaved during the process.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1359-7345
1364-548X
DOI:10.1039/c6cc08182g