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Modular Synthesis of Biaryl‐Substituted Phosphine Ligands: Application in Microwave‐Assisted Palladium‐Catalyzed C–N Cross‐Coupling Reactions
Author(s) -
Singh Chandani,
Rathod Jayant,
Jha Vishwajeet,
Panossian Armen,
Kumar Pradeep,
Leroux Frédéric R.
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500962
Subject(s) - chemistry , phosphine , palladium , steric effects , regioselectivity , catalysis , coupling reaction , combinatorial chemistry , bromine , photochemistry , organic chemistry
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.