2321-92-8

Upstream product

• 67277-15-0 N-phenyl α-phenyl aminomethyldiphenylphosphine 
• 4559-70-0 Diphenylphosphine oxide 
• 1750-36-3 (E)-N-benzylidenebenzenamine 
• 538-51-2 benzylidene phenylamine 
• 829-85-6 diphenylphosphane 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 62-53-3 aniline 
• 539-30-0 1-(ethoxymethyl)benzene 
• 103-50-4 dibenzyl ether 
• 100-52-7 benzaldehyde 

Relevant academic research and scientific papers

C–H Bond Functionalization of 1,4-Benzoquinone by Silver-Mediated Regioselective Phosphination and Amination Reactions

The one-pot synthesis of 2,5-bis(diarylphosphoryl)-3,6-bis(arylamino)cyclohexa-2,5-diene-1,4-diones has been achieved by AgI-mediated full C–H functionalization of 1,4-benzoquinone (BQ) through regioselective dual phosphination and amination reactions. BQ, diarylphosphine oxides [SPOs, Ar2PH(=O)], and imines reacted to give the products under mild conditions. 1,4-Naphthoquinone (NQ) could also be used instead of BQ. When aniline was used instead of the corresponding imine, a lower yield of the desired product was obtained. In the absence of Ag2CO3, hydrophosphinylation of the imine by the SPO occurred as a competitive side-reaction. AgI plays versatile roles in this reaction, as a mediator for facilitating the consecutive additions of Ar2P(=O)– and aniline to the related β-carbon atoms of BQ, as an oxidant of hydroquinone (HQ) intermediates to form the substituted BQ counterpart, and as an inhibitor of the hydrophosphinylation side-reaction of the imine by the SPO. The X-ray crystal structures of several new products have been determined. A reaction mechanism is also proposed based on the experimental results.

TEMPO-Catalyzed Aminophosphinoylation of Ethers via Tandem C(sp3)-H and C(sp3)-O Bond Cleavage

A new TEMPO-catalyzed aminophosphinoylation of ethers with amines and H-phosphine oxides was developed for the synthesis of α-aminophosphine oxides. This metal-free aminophosphinoylation reaction could be conducted under mild conditions through tandem C(sp3)-H and C(sp3)-O bond cleavage. The present method offers a facile and efficient approach to broad range of α-aminophosphine oxide derivatives in moderate to good yields with excellent functional group tolerance.

Addition of borane-protected secondary phosphines to imines. A route to protected mono-N-substituted-α-aminophosphines

Addition of a secondary phosphine-borane adduct to imines was examined in order to improve the synthesis of mono-N-substituted-α-aminophosphines. The reaction demonstrates, for the first time, successful addition of a phosphine-borane to a multiple carbon-nitrogen bond. The process tolerates a range of substituents on the imine and results in an efficient formation of a borane-protected α-aminophosphine. Borane protects the aminophosphine and improves the reliability of the Mannich-like phosphine addition to imines. (C) 2000 Elsevier Science Ltd.

Hydrophosphination of Activated Alkenes by a Cobalt(I) Pincer Complex

Herein we report the synthesis of three heteroleptic first-row transition metal(II) complexes containing carbazolido NNN pincer ligands and conversion to the corresponding metal(I)-carbonyl complexes via a reductive carbonylation route. These complexes are precatalysts for the hydrophosphination of activated alkenes, affording a cobalt-catalysed hydrophosphination process that solely and selectively yields the β addition (anti-Markovnikov) product. The scope of this transformation has been investigated using a variety of activated alkenes. Isolation and characterisation of substrate-coordinated intermediates reveal available coordination sites, which provide insight into the proposed catalytic cycle. (Figure presented.).

Silver-mediated aminophosphinoylation of propargyl alcohols with aromatic amines and H-phosphine oxides leading to α-aminophosphine oxides

A new silver mediated aminophosphinoylation of propargyl alcohols with aromatic amines and H-phosphine oxides for the construction of α-aminophosphine oxides has been developed. The C[sbnd]N and C[sbnd]P bond could be efficiently formed in one pot operati

Preparation method of alpha-amino-phosphine oxide compound

The invention belongs to the field of organic synthesis, and specifically discloses a preparation method of an alpha-amino-phosphine oxide compound. The method includes the following steps that primary amine, a diarylphosphate oxide compound, ethers and a

The synthesis of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides by the microwave-assisted Pudovik reaction

A family of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides was synthesized by the microwave-assisted solvent-free addition of dialkyl phosphites and diphenylphosphine oxide, respectively, to imines formed from benzaldehyde derivatives and primary amines. After optimization, the reactivity was mapped, and the fine mechanism was evaluated by DFT calculations. Two α-aminophosphonates were subjected to an X-ray study revealing a racemic dimer formation made through a N-H?O=P intermolecular hydrogen bridges pair.

Preparation of α-aminophosphines on solid support: Model studies and parallel synthesis

On-resin assembly of phosphine ligands represents a formidable challenge. Following model solution studies, we developed two synthetic routes for α-aminophosphine synthesis on solid support. The ligands are prepared via the Mannich reaction of the resin-bound aldehyde, amine and diphenylphosphine with very good yield and purity. Alternatively, the amine can serve as the anchoring building block. The ligands were qualitatively and quantitatively analyzed using gel-phase 31P and 13C NMR techniques. The studies culminated in the parallel synthesis of a 40-member library of borane-protected α-aminophosphines.