The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthesis of phosphoörganic aromatic compounds with lithium reagents》. Authors are Mikhailov, B. M.; Kucherova, N. F..The article about the compound:Tri(naphthalen-1-yl)phosphinecas:3411-48-1,SMILESS:C1=CC2=C(C=C1)C(=CC=C2)P(C1=CC=CC2=C1C=CC=C2)C1=CC=CC2=C1C=CC=C2).Product Details of 3411-48-1. Through the article, more information about this compound (cas:3411-48-1) is conveyed.
Anthracene does not react with PCl3 in the presence of AlCl3, while PCl5 leads only to Cl derivatives Aryl Li derivatives with P halides in Et2O readily gave P derivatives Thus 3 PhLi and PCl3 gave 61% Ph3P; 1-C10H7Li gave 27% (1-C10H7)3P, m. 278-80°, while 9-phenanthryllithium gave 72% tri-9-phenanthrylphosphine, m. 374-6° (from MePh); 9-anthryllithium gave 20% tri-9-anthrylphosphine, orange-red, m. 270-3°, while 9-bromo-10-anthryllithium gave yellow tris(9-bromo-10-anthryl)phosphine, m. 206-8° (from MePh). Similarly, the Li derivative from 10-bromo-1,2-benzanthracene gave 54.6% tris-(1,2-benzanthr-10-yl)phosphine, yellow, m. 192-4°. POCl3 in Et2O similarly gave 65% Ph3PO, 38% (1-C10H7)3PO, 49% tri-9-phenanthrylphosphine oxide, m. 354-6°, 65% tris-(1,2-benzanthr-10-yl)phosphine oxide, m. 191-3° (from Et2O-benzene); alteration of the proportions of the reagents failed to yield products other than R3PO. Use of C5H10NPOCl2, followed by hydrolysis, gave 64% Ph2PO2H, m. 192-4°, 51% (1-C10H7)2PO2H, m. 198-200°; 9-phenanthryllithium (2 moles/mole chloride) gave 2 acids, 9-phenanthrenephosphonic acid, m. 228-9°, and di-9-phenanthrylphosphinic, acid, giving insoluble Na salt, in 33% and 47% yield, resp.
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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis