88652-75-9Relevant academic research and scientific papers
An efficient method for sterically demanding Suzuki-Miyaura coupling reactions
Zhao, Qing,Li, Chengxi,Senanayake, Chris H.,Tang, Wenjun
supporting information, p. 2261 - 2265 (2013/03/28)
An efficient method for sterically demanding Suzuki-Miyaura coupling reactions has been developed with two catalysts, Pd/BI-DIME (see scheme) and Pd/phenanthrene-based ligand. The Pd/BI-DIME catalyst facilitates the syntheses of extremely hindered biaryls
ortho-Phosphoryl stabilized hypervalent iodosyl- and iodyl-benzene reagents
Meprathu, Bindu V.,Justik, Michael W.,Protasiewicz, John D.
, p. 5187 - 5190 (2007/10/03)
The synthesis and reactivity of a new IBX analogue (2-iodylphenyl)diphenyl- phosphine oxide 10 is described herein along with its analysis by single crystal X-ray diffraction.
Switching on and off metalation sites in triarylphosphines by manipulating substrate coordination
Desponds, Olivier,Huynh, Cyril,Schlosser, Manfred
, p. 983 - 985 (2007/10/03)
The inductive electron-withdrawing effect of the positively charged phosphorus atom in triarylphosphine-borane adducts is largely compensated by the steric congestion caused in its vicinity. Therefore, trihydro(triphenylphosphonio)borate reacts only sluggishly even with superbasic reagents and products derived from ortho-metalated intermediates by their trapping with electrophiles are formed only in poor yield. On the other hand, the borane adducts of (3-anisyl)diphenylphosphine and (3- fluorophenyl)diphenylphosphine can be readily deprotonated at the hetero- adjacent para position and converted into final products in high yields. The phosphorus-remote regioselectivity of these phosphine-borane zwitterions is complementary to that previously observed with the corresponding phosphine oxides.
2,2′-Bis(diphenylphosphino)biphenyl revisited
Desponds, Olivier,Schlosser, Manfred
, p. 257 - 261 (2007/10/03)
The reaction between 2,2′-dilithiobiphenyl and two equivalents of chlorodiphenylphosphine is confirmed to afford equal amounts of 9-phenyl-9-phosphafluorene (2) and triphenylphosphine. 2,2′-Bis(diphenylphosphino)biphenyl (1,1′-biphenyl-2,2′-diylbis(diphenylphosphine) (1)) can be conveniently prepared by Ullmann coupling of 2-iodophenyldiphenylphosphine oxide and subsequent reduction with trichlorosilane.
Phosphides and Arsenides as Metal-Halogen Exchange Reagents. Part 2. Reactions with Aromatic Dihalides
Gillespie, Donal G.,Walker, Brian J.,Stevens, David,McAuliffe, Charles A.
, p. 1697 - 1703 (2007/10/02)
1,2-Dihalogenobenzenes react with two molar equivalents of lithium diphenylphosphide in the presence of furan to give, after oxidation, triphenylphosphine oxide (major) and the corresponding 2-halogenophenyldiphenylphosphine oxide.No trace of furan-dehydrobenzene adduct was observed in these reactions; however, 1- and 2-naphthyldiphenylphosphine oxides (9:4) were detected.These compounds were the major products from the reaction of the furan-dehydrobenzene adduct with diphenylphosphide, although the ratio of 1- to 2-isomers was quite different (1:9) in this case.Reaction of lithium diphenylphosphide with 3,4-dichloronitrobenzene gave tetrachloroazobenzene (40percent) as the only isolated product and attempts to replace 1,2-dihalogenobenzenes with 2-halogenobenzenediazonium salts gave much lower yields of products.Although dehydrobenzene is thought to be involved in many of these reactions, alternative mechanisms also operate, depending on the halides used.The reaction of lithium diphenylarsenide with 1,2-dihalogenobenzenes gave triphenylarsine as the major product and it seems likely that similar mechanisms to those involved in reactions of diphenylphosphide are operating.Surprisingly, dehydrobenzene-furan adduct reacted with diphenylarsenide to give naphthalene in high yield.
