21573-70-6Relevant academic research and scientific papers
Direct Access to α,β-Unsaturated Ketones via Rh/MgCl2-Mediated Acylation of Vinylsilanes
Chen, Zi-Yan,Deng, Xue-Zu,Song, Yang,Xue, Fei,Yamane, Motoki,Yue, Yan-Ni
, p. 12693 - 12704 (2021/09/28)
We report herein the facile and practical construction of α,β-unsaturated ketones via rhodium-catalyzed direct acylation of vinylsilanes with readily available and abundant carboxylic acids. This protocol features access to a diverse array of synthetically useful functionalities with moderate to excellent yields. More importantly, the late-stage functionalization of pharmaceuticals was also realized with synthetically useful yield.
Enones from Acid Fluorides and Vinyl Triflates by Reductive Nickel Catalysis
Pan, Feng-Feng,Guo, Peng,Li, Chun-Ling,Su, Peifeng,Shu, Xing-Zhong
supporting information, p. 3701 - 3705 (2019/05/24)
A nickel-catalyzed reductive coupling between acid fluorides and vinyl triflates has been described. This method provides an efficient access to various enones and avoids the requirement for acyl or vinyl metallic reagents in the conventional approaches.
Ruthenium nitronate complexes as tunable catalysts for olefin metathesis and other transformations
Wdowik, Tomasz,Samojlowicz, Cezary,Jawiczuk, Magdalena,Malinska, Maura,Wozniak, Krzysztof,Grela, Karol
supporting information, p. 674 - 676 (2013/02/25)
Novel ruthenium(ii) complexes were obtained as a result of a stoichiometric reaction of Grubbs' benzylidene second generation catalysts with 3-nitropropene. These stable complexes, formally ruthenaisoxazole N-oxide derivatives, display activity in both me
The intramolecular Morita-Baylis-Hillman-type alkylation reaction
Cran, John W.,Krafft, Marie E.,Seibert, Kimberly A.,Haxell, Thomas F.N.,Wright, James A.,Hirosawa, Chitaru,Abboud, Khalil A.
, p. 9922 - 9943 (2012/02/05)
From the initial development of a homologous Morita-Baylis-Hillman reaction utilizing epoxides as electrophiles, the method was expanded to enable the exclusively organocatalyzed intramolecular allylation of enones and to develop the intramolecular MBH-type alkylation of activated alkenes. We successfully utilized both enones and unsaturated thioesters as the activated alkene component. This work, carried out using stoichiometric amounts of the trialkylphosphine, gave an array of functionalized five- and six-membered carbocycles in high yields. With the cycloalkylation of enones and thioesters, conditions that allowed the use of substoichometric amounts of the phosphine catalyst were developed. As a result both five- and six-membered rings can be formed efficiently with little to no loss in yield upon comparison to yields obtained when stoichiometric amounts of trialkylphosphines were employed. We isolated, for the first time, an MBH-type intermediate exhibiting unprecedented trans geometry of the phosphonium salt and acyl group.
Iron(III)-catalyzed cyclization of alkynyl aldehyde acetals: Experimental and computational studies
Xu, Tongyu,Yang, Qin,Li, Dongpo,Dong, Jinhua,Yu, Zhengkun,Li, Yuxue
supporting information; experimental part, p. 9264 - 9272 (2010/10/03)
FeCl3·6H2O-and FeBr3-catalyzed Prins cyclization/halogenation of alkynyl aldehyde acetals has been realized with acetyl chloride or bromide as halogen source in dichloromethane to afford 2-(1-halobenzylidene or alkylidene)
An alternative approach to aldol reactions: Gold-catalyzed formation of boron enolates from alkynes
Koerner, Cindy,Starkov, Pavel,Sheppard, Tom D.
supporting information; experimental part, p. 5968 - 5969 (2010/07/05)
A new method for enolate generation via the gold-catalyzed addition of boronic acids to alkynes is reported. The formation of boron enolates from readily accessible ortho-alkynylbenzeneboronic acids proceeds rapidly with 2 mol % PPh3AuNTf2
Indium(III)-catalyzed coupling between alkynes and aldehydes to α,β-unsaturated ketones
Miura, Katsukiyo,Yamamoto, Kiyomi,Yamanobe, Aya,Ito, Keisuke,Kinoshita, Hidenori,Ichikawa, Junji,Hosomi, Akira
supporting information; experimental part, p. 766 - 767 (2011/01/09)
The combined use of a catalytic amount of InX3 (X = OTf and NTf2) and 1-butanol was found to be effective in formal alkynealdehyde metathesis. With this catalytic system, aromatic alkynes reacted with aromatic aldehydes to give chalcones in moderate to good yields. Alkynals were efficiently converted into 5- to 7-membered cyclic compounds by intramolecular alkyne-aldehyde coupling.
Cationic P(OPh)3- or PPh3-rhodium(I) complex-catalyzed isomerizations of 5-alkynals to δ-alkynyl ketones, cyclopent-1-enyl ketones, and cyclohexenones
Tanaka, Ken,Sasaki, Kaori,Takeishi, Kenzo,Hirano, Masao
, p. 5675 - 5685 (2008/09/17)
We have developed catalytic isomerizations of 5-alkynals to γ-alkynyl ketones and cyclopent-1-enyl ketones using [Rh{P(OPh)3} 2]BF4 as a catalyst. Cu(OTf)2 and AgBF 4 are also effective catalysts for
1,2-Addition of α,α,α-trichlorotoluene to ketones via a Mg Barbier reaction in DMF: New route to cycloalk-1-en-1-yl and alk-1-en-1-yl phenyl ketones
Aaziz, Akima,Oudeyer, Sylvain,Leonel, Eric,Paugam, Jean Paul,Nedelec, Jean-Yves
, p. 1147 - 1154 (2008/02/01)
The reductive cyclocondensation of α,α,α-trichlorotoluene to enolisable ketones enables the preparation of (cyclo)alken-1-en-1-yl phenyl ketones via the formation of an intermediate chlorooxirane. Copyright Taylor & Francis Group, LLC.
Organocatalysis of the Morita-Baylis-Hillman alkylation using trialkylphosphines
Krafft, Marie E.,Seibert, Kimberly A.
, p. 3334 - 3336 (2008/09/17)
Using a catalytic amount of trialkylphosphines, alkyl halides undergo efficient intramolecular Morita-Baylis-Hillman cyclization. Georg Thieme Verlag Stuttgart.
