Quinoline, 8-(diphenylphosphino)-

Base Information

• Chemical Name: Quinoline, 8-(diphenylphosphino)-
• CAS No.: 28225-52-7
• Molecular Formula: C21H16 N P
• Molecular Weight: 313.339
• Mol file: 28225-52-7.mol

Synonyms:8-(Diphenylphosphino)quinoline;Diphenyl(8-quinolinyl)phosphine

Chemical Property of Quinoline, 8-(diphenylphosphino)-

Chemical Property:

• PSA: 26.48000
• LogP: 3.99300

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Quinoline, 8-(diphenylphosphino)-

There total 7 articles about Quinoline, 8-(diphenylphosphino)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

8-chloroquinoline (611-33-6) + lithium diphenylphosphide (65567-06-8,4541-02-0) → 8-(diphenylphosphino)quinoline (28225-52-7)

Guidance literature:

In tetrahydrofuran; for 14h;

DOI:10.1039/b704615b

Reference yield: 66.0%

8-bromoquinoline (16567-18-3) + chloro-diphenylphosphine (1079-66-9,74391-44-9) → 8-(diphenylphosphino)quinoline (28225-52-7)

Guidance literature:

8-bromoquinoline; With n-butyllithium; In tetrahydrofuran; hexanes; at -78 ℃; for 3h; Inert atmosphere;

chloro-diphenylphosphine; In tetrahydrofuran; hexanes; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1002/chem.201000063

Reference yield: 45.0%

quinolin-8-yl trifluoromethanesulfonate (108530-08-1) + triphenylphosphine (603-35-0) → 8-(diphenylphosphino)quinoline (28225-52-7)

Guidance literature:

With palladium diacetate; In N,N-dimethyl-formamide; at 110 ℃; for 72h;

DOI:10.1016/S0040-4039(00)01850-5

upstream raw materials:

8-bromoquinoline

chloro-diphenylphosphine

quinolin-8-yl trifluoromethanesulfonate

triphenylphosphine

Downstream raw materials:

chlorocarbonyl 8-(diphenylphosphino)quinoline iridium(I)

chlorocarbonyl 8-(diphenylphosphino)quinoline rhodium(I)

chloro(1-naphthyl)[8-(diphenylphosphino)quinoline]nickel(II)

[Pd(8-diphenylphosphanylquinoline)(1-(2,6-dimethylphenylimino)ethyl)Cl]

Refernces

Efficient endo Cycloisomerization of Terminal Alkynols Catalyzed by a New Ruthenium Complex with 8-(Diphenylphosphino)quinoline Ligand and Mechanistic Investigation

10.1002/chem.201703971

This research presents the synthesis and investigation of new ruthenium complexes supported by the P,N-donor ligand 8-(diphenylphosphino)quinoline (DPPQ), specifically focusing on their catalytic efficiency in the endo-cycloisomerization of terminal alkynols to form endo-cyclic enol ethers. The study aimed to develop an efficient homogeneous catalytic method for the synthesis of oxygen-containing heterocycles, which are prevalent in natural products and biologically active molecules. The researchers synthesized several ruthenium complexes, including RuCl2(DPPQ)2 (1), [Ru(μ-Cl)(DPPQ)2]2(BPh4)2 (2), and RuCl(DPPQ)2Py (3). Notably, complex 2, with only 1 mol% loading, demonstrated high catalytic activity, efficiently achieving the 7-endo and 8-endo heterocyclization of aromatic alkynols to yield seven-membered 3-benzoxepine and eight-membered 3-benzo[d]oxocine derivatives. The research concluded that complex 2 is a potent catalyst for endo cycloisomerization, and through stoichiometric reactions, the key intermediate oxacyclocarbene complex 12 was isolated, providing direct evidence of its intermediacy in the catalytic endo-cycloisomerization of alkynols. The study thus contributes to the understanding of the mechanism involved in these catalytic reactions and offers a new avenue for the synthesis of larger oxygen-containing heterocyclic compounds.