115060-54-3Relevant academic research and scientific papers
A new cascade for the one-pot synthesis of linear homoallylic alcohols with an allylic diindium reagent
Hirashita,Yamamura,Kawai,Araki
, p. 387 - 388 (2001)
A new cascade based on a novel allylic diindium reagent has been developed; the indium reagent prepared from 3-bromo-1-iodopropene successively coupled with carbonyl compounds and then with aryl, alkenyl or allyl halides in the presence of a Pd(0) catalys
Titanium-mediated oxidative arylation of homoallylic alcohols
Lee, Kathleen S.,Ready, Joseph M.
supporting information; experimental part, p. 2111 - 2114 (2011/04/23)
E-Substituted styrene derivatives are synthesized from terminal olefins and aryl Grignard reagents through TiIV-mediated oxidative coupling (see scheme). Substrates include homoallylic alcohols containing a range of functional groups and substituted aryl Grignard reagents. The reaction may proceed through aryltitanation followed by β-hydride elimination; reductive elimination of arene occurs from a TiIVH(aryl) intermediate.
Heck reaction of aryl bromides with pent-4-en-2-ol, 2-phenylpent-4-en-2-ol, or hept-6-en-3-ol catalysed by a palladium-tetraphosphine complex
Berthiol, Florian,Doucet, Henri,Santelli, Maurice
, p. 3589 - 3602 (2007/10/03)
The tetraphosphine cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl) cyclopentane in combination with [Pd(η3-C3H 5)Cl]2 affords a very efficient catalyst for the Heck reaction of aryl bromides with pent-4-en
Barbier/Grignard-type allylation or benzylation mediated by the mischmetall/SmI2(cat.) system
Di Scala, Aurore,Garbacia, Stefania,Helion, Florence,Lannou, Marie-Isabelle,Namy, Jean-Louis
, p. 2989 - 2995 (2007/10/03)
Barbier- and Grignard-type allylation and benzylation have been achieved by the use of samarium diiodide in catalytic amounts together with mischmetall (an alloy of the light lanthanides) as a coreductant. Plausible catalytic schemes are proposed. In addition, organocerium and -lanthanum reagents have been obtained from samarium diiodide catalysed reactions between organic halides and cerium or lanthanum metal, giving a new route to organolanthanoid compounds. It also appears that trivalent benzyl and allyl organometallic compounds of cerium and lanthanum are much more stable than the corresponding samarium ones. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
Facile preparation of allylzinc species from allyl bromides and unactivated zinc induced by a catalytic amount of aluminum chloride and their reactions with carbonyl compounds and acetals
Maeda,Shono,Ohmori
, p. 1808 - 1812 (2007/10/02)
The effects of Lewis acids (ZnCl2, AlCl3, BF3, and TiCl4) on the generation of allylzinc species from allyl bromide and unactivated zinc powder in dry tetrahydrofuran (THF) were examined by trapping the organozinc compound with benzaldehyde, that is, Grignard-type allylation of the aldehyde. Among the Lewis acids employed, AlCl3 was found to be the promoter of choice. The allylzinc species preformed in the presence of a catalytic amount of AlCl3 effectively allylated carbonyl compounds. Various aromatic and aliphatic aldehydes as well as ketones were converted into homoallylic alcohols in good to excellent yields. Under the reaction conditions employed, ester, hydroxy, acetal, and aromatic nitro and halide groups were tolerated. In the case of α,β-unsaturated carbonyl compounds, selective 1,2-addition was observed. Substituted allyl bromides such as prenyl, crotyl, cinnamyl, and 2-cyclohexenyl bromides were smoothly converted to the corresponding allylzinc compounds, which reacted with carbonyl compounds to give substituted homoallylic alcohols in excellent yields. The diastereoselectivity in crotylation, cinnamylation, and 2-cyclohexenylation depended upon the structures of both the organic metals and the electrophiles. The origin of the observed selectivity is discussed. The allylation of dimethyl and cyclic acetals accompanied with carbon-oxygen bond cleavage also proceeded in excellent yields provided that two equivalents of AlCl3 was present.
Zinc Mediated Allylation of Aldehydes and Ketones with Cinnamyl Chloride in Aqueous Medium
Sjoeholm, Rainer,Rairama, Riitta,Ahonen, Matthias
, p. 1217 - 1218 (2007/10/02)
The Zn mediated reactions of cinnamyl chloride with aldehydes and ketones in THF-NH4Cl(aq) give-besides α- and γ-addition products-phenyl propenes and dicinnamyls, indicating the presence of radical intermediates in the reaction.
SmCl3-CATALYSED ELECTROCHEMICAL REDUCTIVE ALLYLATION OF KETONES
Hebri, Hassan,Dunach, Elisabet,Perichon, Jacques
, p. 1475 - 1478 (2007/10/02)
A series of homoallylic alcohols was prepared in moderate to good yields from allyl chlorides and ketones, through an electrochemical method using SmCl3 as the catalyst precursor.The electrosyntheses were carried out in undivided cells fitted with a consumable magnesium anode.
Samarium(II)-mediated reaction of allylic phosphate esters with carbonyl compounds: A new method for "Umpolung" of allylic phosphates
Araki, Shuki,Hatano, Masahiro,Ito, Hirokazu,Butsugan, Yasuo
, p. 329 - 336 (2007/10/02)
Allylic phosphates allylate ketones and aldehydes in the presence of samarium(II) iodide.The coupling proceeds with the preservation of the olefin geometry ever, regio- and stereoselectivity are not high.
