4141-48-4Relevant articles and documents
Use of tin derivatives for selective allylation and methylation of halogenophosphorus compounds
Rouand, Herve,Potin, Philippe,Majoral, Jean-Pierre,Bertrand, Guy
, p. 8095 - 8098 (1992)
Palladium(0) catalyzed gem-dimethylation of hexachlorocyclotriphosphazene with tetramethylstannane is described as well as the high yield monoallylation of halogenophosphorus or -boron compounds by allyltrialkylstannanes under photolytic conditions.
Synthesis, Structure, and Solution Studies of Lithiated Allylic Phosphines and Phosphine Oxides
Eren, Nimrod M.,Orr, Samantha A.,Thompson, Christopher D.,Border, Emily C.,Stevens, Michael A.,Blair, Victoria L.
, p. 2080 - 2090 (2020/06/05)
This study reports a new series of 12 α-lithiated allylic phosphines and phosphine oxides. By incorporating Lewis base donors including diethyl ether (Et2O), tetrahydrofuran (THF), N,N,N′,N′,-tetramethylethylenediamine (TMEDA), and N,N,N′,N′,N″,-pentamethyldiethylenetriamine (PMDETA), nine complexes were structurally characterized by single-crystal X-ray crystallography. This includes novel dilithiated allylic phosphine 4 [PhP{CHCHCH2Li(TMEDA)}2] and a rare hemisolvated lithiated phosphine oxide 6 [{Ph2P(O)CHC(Me)CH2Li}2(TMEDA)]. Interestingly, in the solid state, P(III) complexes take advantage of Li-πinteractions to the newly formed delocalized system, in comparison to P(V) complexes where the oxophillic nature of the lithium atom dominates. All 12 complexes were fully characterized in the solution state by multinuclear NMR spectroscopy. DFT calculations on isomers of monomeric lithiated complex 3 [Ph2PCHC(Me)CH2Li(PMDETA)] described the low energy barrier between transition steps of the subtle delocalization of the allylic chain.
Ni-Catalyzed C-P Coupling of Aryl, Benzyl, or Allyl Ammonium Salts with P(O)H Compounds
Yang, Bo,Wang, Zhong-Xia
, p. 1500 - 1509 (2019/02/07)
A methodology that allows for the construction of C-P bonds via the nickel-catalyzed cross-coupling of organoammonium salts with appropriate phosphorus nucleophiles has been developed. Aryl-, pyridyl-, benzyl-, and allyl-ammonium triflates can be employed as the electrophiles. The employed phosphorus-based nucleophiles included diaryl/dibutyl phosphine oxide, dialkyl phosphonates, and ethyl phenylphosphinate. Functional groups OMe, CN, CF3, F, Cl, C(O)NMe2, and C(O)tBu were tolerated.
C-P bond-forming reactions via C-O/P-h cross-coupling catalyzed by nickel
Yang, Jia,Chen, Tieqiao,Han, Li-Biao
supporting information, p. 1782 - 1785 (2015/03/04)
The first Ni-catalyzed C-O/P-H cross-coupling producing organophosphorus compounds is disclosed. This method features wide generality in regard to both C-O and P-H compounds: for C-O compounds, the readily available alcohol derivatives of aryl, alkenyl, benzyl, and allyl are applicable, and for P-H compounds, both >PV(O)H compounds (secondary phosphine oxide, H-phosphinate, and H-phosphonate) and hydrogen phosphines (>PIIIH) can be used as the substrates. Thus, a variety of valuable C(sp2)-P and C(sp3)-P compounds can be readily obtained in good to excellent yields by this new strategy.
