54322-62-2Relevant articles and documents
A convenient synthesis of unsymmetrical pinacols by coupling of structurally similar aromatic aldehydes mediated by low-valent titanium
Duan, Xin-Fang,Feng, Jian-Xia,Zi, Guo-Fu,Zhang, Zhan-Bin
experimental part, p. 277 - 282 (2009/06/24)
The one-pot, selective cross pinacol-type couplings between two structurally similar aromatic aldehydes promoted by low-valent titanium generated unsymmetrical pinacols in moderate to good isolated yields in an erythrolthreo ratio of up to 91:9. This synt
Novel and efficient Ni-mediated pinacol coupling of carbonyl compounds
Shi, Lei,Fan, Chun-An,Tu, Yong-Qiang,Wang, Min,Zhang, Fu-Min
, p. 2851 - 2855 (2007/10/03)
It was firstly found that the Rieke Ni generated in situ was able to promote the pinacol coupling of various carbonyls efficiently. Based on this information, another catalytically effective, cheaper and more convenient NiCl2(Cat.)/Mg/TMSCl system was designed and developed further successfully. The interesting single-electron transfer (SET) mechanisms for the coupling reactions were proposed. Additionally, the DL/meso diastereoselectivity and some additive effects were also explained in terms of the proposed mechanisms.
Alkylative Reduction of Titanium(IV) Isopropoxide with EtMgBr: Convenient Method for the Generation of Subvalent Titanium Alkoxide Reagents and their Reactivity in Pinacol Coupling Reactions
Matiushenkov, Evgenii A.,Sokolov, Nikolai A.,Kulinkovich, Oleg G.
, p. 77 - 80 (2007/10/03)
The composition of the gaseous products from the reaction of Ti(IV) isopropoxide with ethylmagnesium bromide in diethyl ether evidences the formation of subvalent titanium isopropoxide species in various oxidation states depending on relative amounts of the reactants. Reaction of titanium(IV) isopropoxide with one equivalent of the Grignard reagent gives presumably titanium(III) isopropoxide. The latter is generated as a result of disproportionation of starting Ti(IV) species and titanium(II) isopropoxide-ethene complex which is formed as a result of ethane extrusion from diethyltitanium(IV) isopropoxide. Titanium(III) isopropoxide prepared by this way transforms the aldehydes and the aromatic ketones into the corresponding pinacols in good yields.