4a,8a-Azaboranaphthalene-4-yl phosphine ligands: synthesis and electronic modulation in Suzuki–Miyaura coupling reactions

Abstract

Design, synthesis and characterization of new BN-aromatic phosphine ligands are presented, demonstrating moderate catalytic activity in Suzuki reactions of C–Cl bond.

The State of the Art in Azaborine Chemistry: New Synthetic Methods and Applications

“…Additionally, copper-catalyzed phosphination produced 17 , which served as an effective ligand for difficult Suzuki—Miyaura coupling reactions involving electron-deficient aryl chlorides (Scheme 8). 32…”

Six-Membered Rings With Two or More Heteroatoms With at Least One Boron

“…The azaborine unit has also recently been used in the synthesis of new ligands for transition-metal-based catalysis. 179,180 A particular utility of 1,3-dioxa-5-aza-2,4,6-triborinate featuring a B 3 NO 2 heterocycle in dehydrative amidation of carboxylic acids and in catalytic oligopeptide synthesis was described. 181,182 .…”

Selectivity in the Elaboration of Bicyclic Borazarenes

“…1‐Iodo‐9,10‐borazaronaphthalene has been shown to be a suitable electrophile for an array of metal‐catalyzed transformations, in particular couplings with alkynes in Sonogashira reactions, electron‐rich and electron‐poor arylboronic acids in Suzuki reactions, and is a viable substrate in Heck reactions. Additionally, copper‐catalyzed phosphorylation of 1‐iodo‐9,10‐borazaronaphthalene has been applied to develop competent ligands for Suzuki reactions [35] …”