3389-75-1

Upstream product

• 594-19-4 tert.-butyl lithium 
• 184414-26-4 2-(o-iodophenethyl) diphenylphosphinite 
• 1707-03-5 diphenyl-phosphinic acid 
• 622-24-2 2-phenylethyl chloride 
• 60-12-8 2-phenylethanol 
• 4559-70-0 Diphenylphosphine oxide 
• 1079-66-9 chloro-diphenylphosphine 
• 26059-40-5 2-(2-iodophenyl)ethan-1-ol 
• 1499-21-4 Diphenylphosphinic chloride 

Relevant academic research and scientific papers

A solvent-free method for the preparation of phosphinates from P(O)-OH compounds with alkyl chlorides

Herein, a new solvent-free synthetic method using P(O)-OH compound and alkyl chloride for phosphinate compounds is disclosed. This transformation proceeds smoothly under the promotion of a lone base and presents the advantages of an easily available raw material source, a simple post treatment process, good functional group tolerance and high reaction efficiency. Good yield was obtained when the reaction was magnified to gram scale, and the molar ratio of P(O)-OH compounds and alkyl chlorides can be decreased to 1:2. This protocol provides a practical method for the preparation of phosphorus derivatives. Furthermore, the reaction mechanism was explored by means of 31P NMR.

A phosphoryl radical-initiated Atherton-Todd-type reaction under open air

A phosphoryl radical-initiated Atherton-Todd-type reaction using air as the radical initiator and CHCl3 as the halogenating reagent for the phosphorylation of alcohols, phenols, and amines has been developed. This novel transformation provides a highly efficient route to important phosphinates, phosphinic amides, and phosphoramidates in up to 99% yield with a broad substrate scope under very mild conditions (48 examples).

Method for synthesis of organophosphorus compound by photo-induced iodine catalyzed Atherton-Todd reaction

The invention belongs to the technical field of organic synthesis, discloses a method for synthesis of organophosphorus compound by photo-induced iodine catalyzed Atherton-Todd reaction. The method comprises the following steps: a compound shown as formula II and a nucleophilic reagent are subjected to reaction for 24 hours in a dichloromethane solvent, an oxygen atmosphere, under irradiation condition of room temperature and the action of a halogenated reagent I2, then the organophosphorus compound shown as the formula II is obtained through washing, drying, separating and purifying. According to the the method provided by the invention, compared with traditional Atherton-Todd reaction, no catalysis of metal is needed,no addition of alkali is needed, reaction environment such as metal, high temperature and strong base is replaced, a series of organophosphorus compounds can be synthesized by catalyzing a variety of substrates under the irradiation condition of room temperature, and hasthe advantages of good universality, short reaction time and higher yield.

Perfluoroalkanosulfonyl fluoride-assisted Atherton–Todd-like reaction of diphenylphosphine oxide with alcohols under air generating diphenylphosphinate esters

An efficient method for the synthesis of diphenylphosphinate esters via the Atherton–Todd-like reaction of diphenylphosphine oxide with alcohols assisted by perfluoroalkanosulfonyl fluoride in the presence of triethylamine under air is achieved affording the corresponding diphenylphosphinate esters in moderate to good yields of 52–78%. The protocol features the use of non-toxic and stable perfluoroalkanosulfonyl fluoride and metal-free reaction conditions.

Iron-catalyzed clean dehydrogenative coupling of alcohols with P(O)-H compounds: A new protocol for ROH phosphorylation

An efficient oxygen-phosphoryl bond-forming reaction via iron-catalyzed cross dehydrogenative coupling has been developed. This transformation proceeds efficiently under oxidant- and halide-free reaction conditions with H2 liberation, and represents a straightforward method to prepare valuable organophosphoryl compounds from the readily available alcohols and P(O)-H compounds.

Synthesis of new organophosphorus compounds using the atherton-todd reaction as a versatile tool

This article discusses the behavior of seven organophosphorus compounds under Atherton-Todd conditions. Therefore, the reactivity and selectivity of different (phen)oxaphosphinines, dioxaphosphinines, dioxaphosphinanes, and diphenylphosphine oxide with three nucleophiles were systematically studied. The results prove the versatility of the Atherton-Todd reaction to a broad range of organophosphorus compounds with different phosphorus environments and reactive Pi-H bonds. The nucleophiles studied in this article were chosen as model substrates for amines and alcohols. Because organophosphorus molecules are important and versatile compounds, for a broad field of applications, novel synthetic approaches are of interest to both academia and industry. As an example, the single-step synthesis of the bridged 1,3-phenylene bis(diphenylphosphinate) with potential flame-retardant properties was added to this study. In addition, the reaction is utilized for the synthesis of a novel organophosphorus anhydride.

β elimination of a phosphonate group from an alkoxyl radical - Intramolecular acylation using acylphosphonate derivatives as carbonyl group acceptors

The possibility of β elimination of a phosphonate group in radical reactions was studied. The facile β elimination of the phosphonate group from an alkoxyl radical was observed for the first time, whereas the β elimination of the phosphonate group from an

The endocyclic restriction test: Investigation of the geometries of nucleophilic substitution at phosphorus(III) and phosphorus(V)

Double labeling has been used under the endocyclic restriction test to show that transfers of phosphorus from oxygen to carbon in the conversions of lithio phosphinite 1 to alkoxy phosphine 8, of lithio phosphinite 2 to alkoxy phosphine 9, of lithio phosphinate 3 to alkoxy phosphine oxide 10, and of lithio phosphinite borane 4 to alkoxy phosphine borane 11 proceed in an intramolecular fashion. The transfers of stereogenic phosphorus in the conversions of lithio phosphinite (R)-5 to alkoxy phosphine (R)-12, of lithio phosphinate (S)-6 to alkoxy phosphine oxide (S)-13, and of lithio phosphinite borane (R)-7 to alkoxy phosphine borane (R)-14 proceed with retention of stereochemistry at phosphorus. These results rule out the classic in-line S(N)2 pathway and the geometrically equivalent in-line addition-elimination pathway for these endocyclic transfers of phosphorus. The most likely pathway for these nucleophilic substitutions at phosphorus is initial apical nucleophilic attack followed by pseudorotation and elimination of the apical alkoxy leaving group.