169694-34-2Relevant articles and documents
Rhenium complex-catalyzed carbon-carbon formation of alcohols and organosilicon compounds
Umeda, Rui,Jikyo, Toshifumi,Toda, Kazuki,Osaka, Issey,Nishiyama, Yutaka
, p. 1121 - 1124 (2018)
The coupling reactions of allylic and benzylic alcohols and allyltrimethylsilane are efficiently catalyzed by a rhenium complex to give the corresponding 1,5-dienes and alkenes in moderate to good yields. Similarly, alcohols were coupled with ketene silyl acetals to form the corresponding esters.
Fluorinated alcohols as promoters for the metal-free direct substitution reaction of allylic alcohols with nitrogenated, silylated, and carbon nucleophiles
Trillo, Paz,Baeza, Alejandro,Najera, Carmen
, p. 7344 - 7354 (2012/10/30)
The direct allylic substitution reaction using allylic alcohols in 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) and 2,2,2-trifluoroethanol (TFE) as reaction media is described. The developed procedure is simple, works under mild conditions (rt, 50 and 70 °C), and proves to be very general, since different nitrogenated nucleophiles and carbon nucleophiles can be used achieving high yields, especially when HFIP is employed as solvent and aromatic allylic alcohols are the substrates. Thus, sulfonamides, carbamates, carboxamides, and amines can be successfully employed as nitrogen-based nucleophiles. Likewise, silylated nucleophiles such as trimethylsilylazide, allyltrimethylsilane, trimethylsilane, and trimethylsilylphenylacetylene give the corresponding allylic substitution products in high yields. Good results for the Friedel-Crafts adducts are also achieved with aromatic compounds (phenol, anisole, indole, and anilines) as nucleophiles. Particularly interesting are the results obtained with electron-rich anilines, which can behave as nitrogenated or carbon nucleophiles depending on their electronic properties and the solvent employed. In addition, 1,3-dicarbonyl compounds (acetylacetone and Meldrum's acid) are also successfully employed as soft carbon nucleophiles. Studies for mechanism elucidation are also reported, pointing toward the existence of carbocationic intermediates and two working reaction pathways for the obtention of the allylic substitution product.
Indium(i)-catalyzed alkyl-allyl coupling between ethers and an allylborane
Dao, Hai Thanh,Schneider, Uwe,Kobayashi, Shu
, p. 692 - 694 (2011/03/22)
An efficient method for alkyl-allyl cross-coupling between ethers and a 9-BBN-derived allylborane catalyzed by indium(i) triflate has been developed. The allylborane proved to be essential to obtain the desired products in high yields. The reaction displayed good substrate scope including high functional group tolerance. The Royal Society of Chemistry 2011.