Synthesis of Phosphabenzenes by an Iron‐Catalyzed [2+2+2] Cycloaddition Reaction of Diynes with Phosphaalkynes

Abstract

A method for the synthesis of phosphabenzenes under iron catalysis is described. Thus, the FeI2 -catalyzed [2+2+2] cycloaddition of diynes with phosphaalkynes in m-xylene gave a variety of phosphabenzenes in good to high yields (up to 87 % yield).

Multicomponent syntheses of 5- and 6-membered aromatic heterocycles using group 4–8 transition metal catalysts

“…36 ). 139 Tri- and tetrasubstituted phosphabenzenes 77 can be synthesized from tethered diynes 76 and phosphaalkynes with either tertiary alkyl or bulky siloxide (TBDPS) substituents—the latter of which could be deprotected to 2-phosphaphenols. 140 Notably, group 9 metal catalysts also exhibited catalytic activity, however in much lower yields and with poorer chemoselectivity against trimerization of alkyne.…”

Reactivity Studies of Phosphinines: The Selenation of Diphenyl-Phosphine Substituents and Formation of a Chelating Bis(Phosphinine) Palladium(II) Complex

“…Phosphinines are the phosphorus analogue of pyridine. The initial discovery of 2,4,6-triphenylphosphinine by Märkl [1] and the parent, unsubstituted phosphinine by Ashe [2] are now landmarks in low-coordinate main group chemistry and continue to inspire new research in the field [3,4]. Recent developments have focused on the use of phosphinines as ligands [5][6][7][8][9][10], particularly in homogeneous catalysis [11][12][13][14][15] where they show interesting differences to conventional phosphine ligands.…”

2‐(Trimethylsilyl)‐λ3‐Phosphinine: Synthesis, Coordination Chemistry, and Reactivity

“…To date, several synthetic routes to phosphinines have been reported in the literature . They individually offer the possibility to realize different substitution patterns and to introduce functionalities into specific positions of the 6‐membered, aromatic ring.…”