38828-95-4Relevant academic research and scientific papers
An improved 1,3-diene synthesis from alkyne and ethylene using cross-enyne metathesis
Tonogaki, Keisuke,Mori, Miwako
, p. 2235 - 2238 (2002)
Synthesis of 1,3-diene from alkyne and ethylene (1 atm) was improved using ruthenium carbene complex 1b having heterocyclic carbene as a ligand. In this reaction, the heteroatom at the propargylic position was not required, although the reaction of alkyne
A new facile synthesis of 2-substituted 1,3-butadiene derivatives via palladium-catalyzed cross-coupling reaction of 2,3-alkadienyl carbonates with organoboron compounds
Moriya,Moriya, Tsukasa,Furuuchi,Furuuchi, Toshinari,Miyaura,Miyaura, Norio,Suzuki,Suzuki, Akira
, p. 7961 - 7968 (1994)
A synthesis of 2-aryl, 2-(1-alkenyl)-, and 2-alkyl-1,3-butadiene derivatives (2) by the palladium-catalyzed cross-coupling reaction of 2,3-butadienyl carbonates (1) with 9-alkyl-9-bicyclo[3.3.1]nonanes (9-alkyl-9-BBN), 1-alkenylboronic acids, or arylboron
A General Nickel-Catalyzed Kumada Vinylation for the Preparation of 2-Substituted 1,3-Dienes
Fiorito, Daniele,Folliet, Sarah,Liu, Yangbin,Mazet, Clément
, p. 1392 - 1398 (2018/02/14)
The identification of two nickel(II) precatalysts for the preparation of 2-substituted 1,3-dienes by a Kumada cross-coupling between vinyl magnesium bromide and vinyl phosphates is described. This is noteworthy as engaging only one vinyl derivative in a transition-metal-catalyzed cross-coupling reaction is already reputedly challenging. Salient features of this method are its operational simplicity, the mild reaction conditions, the low catalyst loadings, the short reaction times, its scalability, and the use of stoichiometric quantities of each coupling partner. The tolerance of the two nickel catalysts to an important number of reactive functional groups and their compatibility with structurally complex molecular architectures has been extensively delineated. A Negishi variant of the reaction has been developed for even more sensitive organic functions such as ester or nitrile. Several other conjugated 1,3-dienes with various substitution patterns have been prepared by combining commercial alkenyl Grignard reagents and/or readily available alkenyl enol phosphates. Proper choice of the nickel catalyst and the reaction temperature gave access to a variety of different olefin isomers with high levels of stereocontrol. Overall, this approach affords conjugated dienes that would not be accessible otherwise and therefore provides a valuable complement to existing methods.
Exploring Site Selectivity of Iridium Hydride Insertion into Allylic Alcohols: Serendipitous Discovery and Comparative Study of Organic and Organometallic Catalysts for the Vinylogous Peterson Elimination
Li, Houhua,Fiorito, Daniele,Mazet, Clément
, p. 1554 - 1562 (2017/08/15)
The vinylogous Peterson elimination of a broad range of primary, secondary, and tertiary silylated allylic alcohols by two distinct and complementary catalytic systems - a cationic iridium complex and a Br?nsted acid - is reported. These results are unexpected. Nonsilylated substrates are typically isomerized into aldehydes and silylated allylic alcohols into homoallylic alcohols with structurally related iridium complexes. Although several organic acids and bases are known to promote the vinylogous Peterson elimination, the practicality, mildness, functional group tolerance, and generality of both catalysts are simply unprecedented. Highly substituted C=C bonds, stereochemically complex scaffolds, and vicinal tertiary and quaternary (stereo)centers are also compatible with the two methods. Both systems are stereospecific and enantiospecific. After optimization, a vast number of dienes with substitution patterns that would be difficult to generate by established strategies are readily accessible. Importantly, control experiments secured that traces of acid that may be generated upon decomposition of the in situ generated iridium hydride are not responsible for the activity observed with the organometallic species. Upon inspection of the reaction scope and on the basis of preliminary investigations, a mechanism involving iridium-hydride and iridium-allyl intermediates is proposed to account for the elimination reaction. Overall, this study confirms that site selectivity for [Ir-H] insertion across the C=C bond of allylic alcohols is a key parameter for the reaction outcome.
Diversity-oriented synthesis of biaryl derivatives using cross-enyne metathesis, diels-alder reaction, and suzuki-miyaura cross-coupling as key steps
Kotha, Sambasivarao,Seema, Vittal
, p. 2329 - 2334 (2011/10/30)
Biaryl derivatives have been prepared by utilizing cross-enyne metathesis, Diels-Alder reaction followed by aromatization. These biaryl derivatives are further functionalized via Suzuki-Miyaura cross-coupling reaction to generate functionalized terphenyl derivatives. Georg Thieme Verlag Stuttgart - New York.
Regiodiverse three-component synthesis of arenes
Danz, Michael,Hilt, Gerhard
supporting information; experimental part, p. 303 - 308 (2011/04/18)
A ruthenium-catalyzed enyne metathesis reaction followed by a cobalt-catalyzed Diels-Alder reaction and oxidation of the dihydroaromatic intermediate generates the two regioisomeric aromatic products in good overall yields in a one-pot procedure. The regiochemistry of the cycloaddition can be controlled by the ligand choice on the cobalt catalyst to generate the product with the 1,3,5-or the 1,2,4-substitution pattern predominantly. The high functional group tolerance was used to generate bifunctionalized building blocks and finally an unprecedented regioselective Scholl reaction is described.
Enantioselective construction of all-carbon quaternary centers by branch-selective Pd-catalyzed allyl-allyl cross-coupling
Zhang, Ping,Le, Hai,Kyne, Robert E.,Morken, James P.
, p. 9716 - 9719 (2011/08/04)
The Pd-catalyzed cross-coupling of racemic tertiary allylic carbonates and allylboronates is described. This reaction generates all-carbon quaternary centers in a highly regioselective and enantioselective fashion. The outcome of these reactions is consistent with a process that proceeds by way of 3,3′-reductive elimination of bis(η1-allyl)palladium intermediates. Strategies for distinguishing the product alkenes and application to the synthesis of (+)-α-cuparenone are also described.
Enantioselective (Formal) Aza-diels-alder reactions with non-danishefsky-type dienes
Tambar, Uttam K.,Lee, Sharon K.,Leighton, James L.
supporting information; experimental part, p. 10248 - 10250 (2010/09/05)
Enantioselective (formal) aza-Diels-Alder reactions between acylhydrazones and non-Danishefsky-type dienes have been developed. The reactions are promoted by a simple and economical chiral silicon Lewis acid and are typically conducted at ambient temperature. Both glyoxylate- and aliphatic aldehyde-derived hydrazones may be employed, as may variously substituted dienes, leading to the synthesis of a diverse array of tetrahydropyridines with good to excellent levels of enantioselectivity.
Palladium-catalyzed cross-couplings of 1,3-butadien-2-yl species with organoindiums generated from allenylmethyl bromide and indium
Kim, Sundae,Seomoon, Dong,Lee, Phil Ho
supporting information; experimental part, p. 1873 - 1875 (2009/10/17)
An organoindium generated from the reaction of indium with allenylmethyl bromide is an efficient nucleophile in Pd-catalyzed cross-couplings, producing 1,3-butadienes; cross-couplings followed by [4 + 2] cycloadditions gave six-membered carbocycles in a o
Palladium-catalyzed 1-methylene-2-propenylation reactions of aryl bromides with 3,4-alkadien-1-ols via carbon-carbon bond cleavage for the synthesis of 2-aryl-1,3-butadiene derivatives
Imoto, Junichi,Hayashi, Sayuri,Hirano, Koji,Yorimitsu, Hideki,Oshima, Koichiro
experimental part, p. 393 - 400 (2009/06/28)
A method for the synthesis of 2-aryl-1,3-alkadienes has been developed. Treatment of aryl bromides with 3,4-alkadien-1-ols in the presence of a palladium catalyst results in 1-methylene-2-propenyl group transfer to aryl bromides. Taking advantage of palla
