Modular synthesis of biaryl-substituted phosphine ligands: application in microwave-assisted palladium-catalyzed C-N cross-coupling reactions

TitleModular synthesis of biaryl-substituted phosphine ligands: application in microwave-assisted palladium-catalyzed C-N cross-coupling reactions
Publication TypeJournal Article
Year of Publication2015
AuthorsSingh, C, Rathod, J, Jha, V, Panossian, A, Kumar, P, Leroux, FR
JournalEuropean Journal of Organic Chemistry
Issue29
Pagination6515-6525
Date PublishedOCT
ISSN1434-193X
KeywordsBiaryls, Cross-coupling, Homogeneous catalysis, Microwave chemistry, Palladium, Phosphines, synthetic methods
Abstract

Biaryl-substituted monophosphine-based ligands have been synthesized by transition-metal-free ARYNE cross-coupling reaction of aryllithiums with 1,2-dibromobenzene and subsequent regioselective functionalization through bromine-lithium interconversion. These ligands were employed in palladium-catalyzed C-N bond-forming reactions. The reaction was found to be general with wide substrate applicability. A wide variety of both primary and secondary amines were successfully coupled with an array of differently substituted halobenzenes under microwave irradiation to give the expected products in good to excellent yields. A number of biaryl-substituted phosphine ligands screened for the coupling reaction showed that steric bulk and the electronic properties of substituents on phosphorus play a crucial role in governing the catalytic activity of C-N cross-coupling reactions.

DOI10.1002/ejoc.201500962
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

3.068

Divison category: 
Organic Chemistry