5397-27-3Relevant academic research and scientific papers
Visible-Light-Driven, Metal-Free Divergent Difunctionalization of Alkenes Using Alkyl Formates
Zheng, Ming,Hou, Jing,Zhan, Le-Wu,Huang, Yan,Chen, Ling,Hua, Li-Li,Li, Yan,Tang, Wan-Ying,Li, Bin-Dong
, p. 542 - 553 (2021/01/14)
In recent decades, difunctionalization of alkenes has received considerable attention as an efficient and straightforward way to increase molecular complexity. However, examples of the difunctionalization of alkenes initiated by the intermolecular addition of alkoxycarbonyl radicals providing substituted alkanoates are still rare. Herein, we present the visible light-driven metal-free divergent difunctionalization of alkenes triggered by the intermolecular addition of alkoxycarbonyl radicals under ambient conditions. Employing alkyl formates as precursors of alkoxycarbonyl radicals and 4CzIPN as the photocatalyst, a variety of substituted alkanoates, including β-alkoxy, β-hydroxy, β-dimethoxymethoxy, and β-formyloxy alkanoates, could be facilely accessed with high functional group tolerance and high efficiency. Moreover, the mechanism study revealed that β-hydroxy alkanoates were generated by a selective decomposition of orthoformates promoted by the N-alkoxyazinium salt.
A Ball-Milling-Enabled Reformatsky Reaction
Cao, Qun,Stark, Roderick T.,Fallis, Ian A.,Browne, Duncan L.
, p. 2554 - 2557 (2019/06/17)
An operationally simple one-jar one-step mechanochemical Reformatsky reaction using in situ generated organozinc intermediates under neat grinding conditions has been developed. Notable features of this reaction protocol are that it requires no solvent, no inert gases, and no pre-activation of the bulk zinc source. The developed process is demonstrated to have good substrate scope (39–82 % yield) and is effective irrespective of the initial morphology of the zinc source.
Asymmetric Synthesis of α-Chloro-α-halo Ketones by Decarboxylative Chlorination of α-Halo-β-ketocarboxylic Acids
Iwasa, Seiji,Kitahara, Kazumasa,Mizutani, Haruna,Shibatomi, Kazutaka
supporting information, p. 4385 - 4392 (2019/11/21)
Chiral α-chloro-α-fluoro ketones were synthesized by enantio-selective decarboxylative chlorination of α-chloro-β-ketocarboxylic acids in the presence of a chiral amine catalyst. The reaction yielded the corresponding α-chloro-α-fluoro ketones with modera
RhII-catalyzed [3+2] cycloaddition of 2 H-azirines with N-sulfonyl-1,2,3-triazoles
Zhao, Yun-Zhou,Yang, Hai-Bin,Tang, Xiang-Ying,Shi, Min
supporting information, p. 3562 - 3566 (2015/03/04)
RhII-catalyzed intermolecular [3+2] cycloaddition of 2 H-azirines with N-sulfonyl-1,2,3-triazoles is disclosed, in which a series of fully functionalized pyrroles is produced via rhodium azavinyl carbene intermediates. A distinct feature of this reaction is that the azavinyl carbene serves as a [2 C] equivalent, instead of as [1 C] or aza-[3 C] synthons, which have been reported previously in cyclopropanations and [3 + n] cycloadditions. Moreover, this methodology has also been successfully applied in the total synthesis of URB447 as well as the formal synthesis of Atorvastatin (Lipitor).
Gold-catalyzed synthesis of functionalized pyridines by using 2H-azirines as synthetic equivalents of alkenyl nitrenes
Prechter, Agnes,Henrion, Guilhem,Faudot Dit Bel, Pierre,Gagosz, Fabien
supporting information, p. 4959 - 4963 (2014/05/20)
2H-Azirines are easily synthesized from the corresponding ketones and, despite possessing a C=N bond embedded in a strained three-membered cycle, they are sufficiently stable to be isolated, stored, and manipulated. 2H-Azirines can be regarded as valuable
Rhenium-catalyzed reaction of carbonyl compounds with ketene silyl acetals
Nishiyama, Yutaka,Kaiba, Kenta,Umeda, Rui
experimental part, p. 793 - 795 (2010/03/24)
It was found that rhenium complex is an effective catalyst for the reaction of carbonyl compounds with ketene silyl acetals. A wide range of β-silyloxy esters is obtained by the treatment of carbonyl compounds with ketene silyl acetals in the presence of
Titanium-catalyzed Reformatsky-type reaction
Sgreccia, Laura,Bandini, Marco,Morganti, Stefano,Quintavalla, Arianna,Umani-Ronchi, Achille,Cozzi, Pier Giorgio
, p. 3191 - 3197 (2008/02/08)
A catalytic titanium mediated Reformatsky reaction is presented. The technique employs cyclopentadienyltitaniumdichloride(IV) (10 mol%) in conjunction with Mn (2 equiv.), as the stoichiometric reductant, and (CF3CO)2O (1.5 equiv.), a
One-step deprotonation route to zinc amide and ester enolates for use in aldol reactions and Negishi couplings
Hlavinka, Mark L.,Hagadorn, John R.
, p. 5049 - 5053 (2007/10/03)
Simple amides and esters are conveniently deprotonated by Zn(tmp)2 (tmp = 2,2,6,6-tetramethylpiperidinyl anion) to generate Zn enolates. Enolates formed by this method are suitable for use in aldol reactions that tolerate base-sensitive functional groups. Additionally, the Zn enolates are readily coupled with aryl bromides using typical Pd-catalyzed coupling methods.
Reformatsky reactions with SmI2 in catalytic amount
Orsini, Fulvia,Lucci, Elvira Maria
, p. 1909 - 1911 (2007/10/03)
A substoichiometric protocol for Reformatsky-type addition of α-haloesters, α-haloketones, α-halonitriles, and α-halophosphonates to carbonyl compounds has been developed. β-Hydroxyesters and β-hydroxynitriles were obtained in good to excellent yields.
PREPARATION OF ORGANOZINC HALIDES FROM REACTIVE HALOGEN COMPOUNDS AND THEIR USE
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, (2008/06/13)
A process for preparing organozinc halides in solvents, includes reacting a reactive halogen compound with zinc in one or more carboxylic esters. It is also possible to prepare keto, hydroxyl and amino compounds of organozinc halides obtained in a first step from a reactive halogen compound and zinc in one or more carboxylic esters, wherein the organozinc halide obtained is reacted in a second step with an electrophilic reaction partner and the reaction product of the second step is hydrolyzed in a third step.
