58732-17-5Relevant academic research and scientific papers
Cross-coupling of vinylethylene carbonates with arylboronic acids catalyzed by in situ generated palladium nanoparticles in water
Mao, Yuxue,Zhai, Xing,Khan, Ajmal,Cheng, Jiong,Wu, Xue,Zhang, Yong Jian
supporting information, p. 3268 - 3271 (2016/07/11)
A practical and greener method of the cross-coupling of vinylethylene carbonates (VECs) with arylboronic acids has been described. The coupling reaction was catalyzed by in situ generated palladium nanoparticles (PdNPs) without any ligands and additional stabilizers in water under ambient conditions to provide useful 4-hydroxylprenylarenes and their derivatives in good to high yields.
Tosylated lithium 2-(lithiomethyl)-2-propen-1-olate: A γ-alkoxide allyl sulfone anion in organic synthesis
Alonso, Diego A.,Najera, Carmen,Sansano, Jose M.
, p. 6603 - 6620 (2007/10/02)
Dilithiated 2-(tosylmethyl)-2-propen-1-ol (6) functioned as a nucleophile at the α-position of the allylic anion in reactions with deuterium oxide, alkyl halides, and aldehydes, and in conjugate additions to α,β-unsaturated carbonyl compounds. With nitro-
PALLADIUM CATALYZED COUPLING OF ORGANOSTANNANES WITH VINYL EPOXIDES
Tueting, David R.,Echavarren, Antonio M.,Stille, J. K.
, p. 979 - 992 (2007/10/02)
The coupling reaction of organotin reagents with vinyl epoxides, catalyzed by palladium, takes place at ambient temperatures, regioselectively, giving predominately the 1,4-addition product.Both aryl- and vinylstannanes undergo coupling in high yields, wh
Transition-metal-catalyzed Grignard Reaction of Isoprene Bromohydrin
Araki, Shuki,Ohmura, Masayuki,Butsugan, Yasuo
, p. 1607 - 1608 (2007/10/02)
The coupling reaction of isoprene bromohydrin with aryl and alkyl Grignard reagents catalyzed by tetrakis(triphenylphosphine)palladium(0) selectively gave the vinyl-group-migrated products.
Substitution Reactions of Secondary Halides and Epoxides with Higher Order, Mixed Organocuprates, R2Cu(CN)Li2: Synthetic, Stereochemical, and Mechanistic Aspects
Lipshutz, Bruce H.,Wilhelm, Robert S.,Kozlowski, Joseph A.,Parker, David
, p. 3928 - 3938 (2007/10/02)
Higher order cuprates, represented by the general formula R2Cu(CN)Li2, are readily prepared from copper cyanide and 2 equiv of an organolithium.These novel reagents react readily and efficiently with secondary unactivated iodides and bromides affording products of substitution.Likewise, mono-, di-, and trisubstituted epoxides undergo ring opening leading to the corresponding alcohols in excellent yields.The effects of solvent, temperature, gegenion, and variations in ligands are discussed.Replacement of the second equivalent of RLi by CH3Li strongly encouragestransfer of R over CH3 in R(CH3)Cu(CN)Li2 with halides.Use of PhLi as RRLi in place of one RTLi (i.e.RT(Ph)Cu(CN)Li2) is suggested for oxirane cleavage.The stereochemical implications associated with both couplings are also addressed.
COPPER(I)-CATALYZED REACTION OF ISOPRENE BROMOHYDRIN WITH ORGANOLITHIUM REAGENT
Araki, Shuki,Butsugan, Yasuo
, p. 185 - 186 (2007/10/02)
The reaction of isoprene bromohydrin (1-bromo-2-methyl-3-buten-2-ol) (1) with ethyl-, propyl- and butyllithium in the presence of copper(I) iodide leads to the exclusive formation of the vinyl group migrated 2-alkyl-4-penten-2-ols (3d-3f), in contrast to
