Modular Synthesis of Biaryl‐Substituted Phosphine Ligands: Application in Microwave‐Assisted Palladium‐Catalyzed C–N Cross‐Coupling Reactions. Issue 29 (26th August 2015)

• Record Type: Journal Article
• Authors: Singh, Chandani; Rathod, Jayant; Jha, Vishwajeet; Panossian, Armen; Kumar, Pradeep; Leroux, Frédéric R.
• Is Part Of: European journal of organic chemistry. Issue 29(2015)
• Page Start: 6515
• Page End: 6525
• Publication Date: 2015-08-26
• Subjects: Synthetic methods -- Homogeneous catalysis -- Palladium -- Cross‐cou­pling -- Microwave chemistry -- Biaryls -- Phosphines; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201500962
• Languages: English
• ISSNs: 1434-193X

Abstract

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. Abstract : Biaryl‐substituted monophosphines have been synthesized by transition metal free ARYNE cross‐coupling reactions and subsequent regioselective functionalization through bromine–lithium interconversion. These ligands were employed in palladium‐catalyzed C–N bond‐forming reactions.