74866-28-7Relevant articles and documents
Synthesis method of 2, 2 '-bisdiphenylphosphino-1, 1'-binaphthalene
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, (2020/09/12)
The invention relates to a synthesis method of 2, 2 '-bisdiphenylphosphino-1, 1'-binaphthalene, which is realized by the following steps: step 1, carrying out BUCHERER reaction on 1, 1 '-binaphthyl-2-naphthol to generate 1, 1'-binaphthyl-2, 2 '-diamine; 2, subjecting 1, 1 '-binaphthyl-2, 2'-diamine to a Sandmeyer reaction to generate binaphthyl dibromide; and 3, carrying out a Grignard reaction onthe binaphthyl dibromide and diphenyl phosphine chloride to generate 2, 2 '-bisdiphenylphosphino-1, 1'-binaphthalene (BINAP). Bulk chemical raw materials are used and are low in price and easy to obtain, and the production cost is effectively reduced; the method has the advantages of easily available raw materials, high reaction yield, simple post-treatment, facilitation of industrial amplification, and strong industrial application prospect.
Reconnaissance of reactivity of an Ag(II)SO4 one-electron oxidizer towards naphthalene derivatives
Budniak, Adam K.,Masny, Micha?,Prezelj, Kristina,Grzeszkiewicz, Miko?aj,Gawraczyński, Jakub,Dobrzycki, ?ukasz,Cyrański, Micha? K.,Ko?miński, Wiktor,Mazej, Zoran,Fija?kowski, Karol J.,Grochala, Wojciech,Leszczyński, Piotr J.
supporting information, p. 10742 - 10749 (2017/10/03)
We test divalent silver sulphate, Ag(ii)SO4 as a novel reagent for oxidative coupling of aromatic hydrocarbons under ambient temperature conditions. The applicability of the C(sp2)-C(sp2) coupling protocol is illustrated for naphthalene and its 1-substituted derivatives containing either electron donating (e.g. Me, MeO, or Ph) or electron-withdrawing groups (X = F?I), leading to 4,4′-disubstituted-1,1′-binaphthyls. Coupling of 2-bromo-naphthalene yields a mixture of 2,2′-, 2,7′-, and 7,7′-dibromo-1,1′-binaphthyls together with their trimeric and tetrameric analogues. The coupling of strongly electron-withdrawing 1-CF3-naphthalene provides the 5,5′-disubstituted-1,1′-binaphthyl derivative. The new method does not require the presence of halogen substituents, in contrast to most of the known C-C coupling methods, and it preserves them, if present. Ag(ii)SO4 may be easily electrochemically regenerated from the Ag(i)HSO4 byproduct. However, the C-C coupling method currently suffers from low yields, up to 17%, and it requires further optimization.
A highly diastereoselective route to dinaphtho [c,e][1,2] oxaphosphinines and their application as ligands in homogeneous catalysis
Shuklov, Ivan A.,Dubrovina, Natalia V.,Jiao, Haijun,Spannenberg, Anke,Boerner, Armin
experimental part, p. 1669 - 1680 (2010/07/04)
A new and facile method for the synthesis of 6H-dinaphtho[c,e][1,2] oxaphosphinines starting from dinaphthol (BINOL) is described. The ring-opening of an intermediary dinaphtho[2,1-b;1′,2′-d]furan proceeds with extremely high diastereoselectivity and forms the thermodynamically most stable product. The stereochemistry was elucidated by 31P NMR spectroscopy and X-ray structural analysis. Epimerization at the stereogenic P-centre did not take place. DFT calculations were performed to determine the dihedral angles of several dinaphtho[c,e][1,2]oxaphosphinines and to explain the observed loss of stereochemistry during the total synthesis from, the starting enantiopure BINOL. The synthetic potential of 6-chloro-6H-dinaphtho[c,e][1,2]oxaphosphinine was corroborated in its reactions with phenols to afford the corresponding phosphonites. These were successfully applied as ligands in the Rh-catalysed hydroformylation of three terminal olefins.