22740-01-8Relevant academic research and scientific papers
From insertion to multicomponent coupling: Temperature dependent reactions of arynes with aliphatic alcohols
Thangaraj, Manikandan,Bhojgude, Sachin Suresh,Mane, Manoj V.,Biju, Akkattu T.
supporting information, p. 1665 - 1668 (2016/01/30)
The temperature dependent selectivity switch in the reaction of arynes with aliphatic alcohols in THF has been reported. At -20°C, arynes smoothly insert into the O-H bond of alcohols to form alkyl aryl ethers. Interestingly, at 60°C, a highly selective multicomponent coupling occurs with the solvent THF acting as the nucleophilic trigger affording (4-(alkoxy)butoxy)arenes.
A Novel Class of Tunable Zinc Reagents (RXZnCH2Y) for Efficient Cyclopropanation of Olefins
Lorenz, Jon C.,Long, Jiang,Yang, Zhiqiang,Xue, Song,Xie, Yinong,Shi, Yian
, p. 327 - 334 (2007/10/03)
A class of zinc reagents (RXZnCH2Y) generated with an appropriate organozinc is very effective for the cyclopropanation of olefins. The reactivity and selectivity of these reagents can be regulated by tuning the electronic and steric nature of the RX group on Zn. A reasonable level of enantioselectivity was obtained for the cyclopropanation of unfunctionalized olefins when a chiral (iodomethyl)zinc species was used, providing a valuable approach for the asymmetric cyclopropanation of unfunctionalized olefins.
Exploring new reactive species for cyclopropanation
Yang, Zhiqiang,Lorenz, Jon C.,Shi, Yian
, p. 8621 - 8624 (2007/10/03)
An organozinc species RXZnCH2I generated by reacting Zn(CH2I)2 with RXH was found to be an efficient reagent for the cyclopropanation of olefins at room temperature. A 50.7% ee was obtained for the cyclopropanation of trans-β-methylstyrene when a chiral alcohol was used.
Electrochemical Cyclopropanation of Alkenes Using Dibromomethane and Zinc in CH2Cl2/DMF Mixture
Durandetti, Sylvie,Sibille, Soline,Perichon, Jacques
, p. 3255 - 3258 (2007/10/02)
An efficient electrosynthesis of cyclopropanes from gem-dibromoalkanes and alkenes is achieved in a one-compartment cell fitted with a sacrificial zinc anode.The part played by the anodically generated Zn(II) in the coupling reaction is pointed out, and evidence for the existence of an organozinc species as intermediate is presented.
Palladium(II)-Catalyzed Cyclopropanation of Simple Allyloxy and Allylamino Compounds and of 1-Oxy-1,3-butadienes with Diazomethane
Tomilov, Yu. V.,Kostitsyn, A. B.,Shulishov, E. V.,Nefedov, O. M.
, p. 246 - 248 (2007/10/02)
(Alkyloxymethyl)-, (aminomethyl)-, (2-alkoxyethenyl)-, (2-acetoxyethenyl)-, and (2-siloxyethenyl)cyclopropanes are obtained in high yields by reaction of allyl alcohol or derivatives, allylamines, 1-alkoxy-, 1-acetoxy-, and 1-trimethylsiloxy-1,3-butadienes with diazomethane in dichloromethane/diethylether in the presence of bis(benzonitrile)palladium dichloride.
REACTIONS OF DIAZOALKANES WITH UNSATURATED COMPOUNDS. 8. CATALYTIC CYCLOPROPANATION OF ALLYL ALCOHOLS AND ALLYLAMINES WITH DIAZOMETHANE
Tomilov, Yu. V.,Kostitsyn, A. B.,Dokichev, V. A.,Dzhemilev, U. M.,Nefedov, O. M.
, p. 2518 - 2521 (2007/10/02)
Allyl alcohols and allylamines have been cyclopropanated directly with diazomethane in the presence of palladium compounds to give 60-88percent of cyclopropylmethanols and cyclopropylmethylamines, respectively, almost free from the products of formal insertion of methylene into the heteroatom-hydrogen bond.
