15325-63-0Relevant academic research and scientific papers
Stereospecific Iron-Catalyzed Carbon(sp2)-Carbon(sp3) Cross-Coupling with Alkyllithium and Alkenyl Iodides
Lu, Xiao-Lin,Shannon, Mark,Peng, Xiao-Shui,Wong, Henry N. C.
supporting information, p. 2546 - 2549 (2019/03/26)
An efficient synthetic protocol involving iron-catalyzed cross-coupling reactions between organolithium compounds and alkenyl iodides as key coupling partners was achieved. More than 30 examples were obtained with moderate to good yields and high stereospecificity. Gram-scale and synthetic applications of this procedure are recorded herein to demonstrate its feasibility and potential utilization.
Iron-Catalyzed Vinylic C?H Alkylation with Alkyl Peroxides
Ge, Liang,Jian, Wujun,Zhou, Huan,Chen, Shaowei,Ye, Changqing,Yu, Fei,Qian, Bo,Li, Yajun,Bao, Hongli
supporting information, p. 2522 - 2528 (2018/08/01)
A variety of alkyl peresters and alkyl diacyl peroxides, which are readily accessible from carboxylic acids, are utilized as general primary, secondary, and tertiary alkylating reagents for iron-catalyzed vinylic C?H alkylation of vinyl arenes, dienes, and 1,3-enynes. This transformation affords olefinic products in up to 98 % yield with high E/Z values. A broad range of functionalities, including carboxyl, boronic acid, methoxy, ester, amino, and halides, are tolerated. This protocol provides a facile approach to some olefins that are difficult to access, and hence, offers an alternative to existing systems. The synthetic utility of this method is demonstrated by late-stage functionalization of selected natural-product derivatives.
Stereoretentive Pd-catalyzed kumada-corriu couplings of alkenyl halides at room temperature
Krasovskiy, Arkady L.,Haley, Stephen,Voigtritter, Karl,Lipshutz, Bruce H.
, p. 4066 - 4069 (2014/10/15)
Stereoselective palladium-catalyzed Kumada-Corriu reactions of functionalized alkenyl halides and a variety of Grignard reagents, including those bearing β-hydrogen atoms and sensitive functional groups, can be carried out at room temperature using a new combination of reagents.
Silver-catalyzed regioselective carbomagnesiation of alkynes with alkyl halides and Grignard reagents
Kambe, Nobuaki,Moriwaki, Yuusuke,Fujii, Yuuki,Iwasaki, Takanori,Terao, Jun
supporting information; experimental part, p. 4656 - 4659 (2011/10/18)
A silver-catalyzed carbomagnesiation of alkynes with alkyl halides and Grignard reagents afforded alkenyl Grignard reagents regioselectively, where the alkyl group of the alkyl halide, but not that of the Grignard reagent, was introduced into the alkyne.
Identification of a valuable kinetic process in copper-catalyzed asymmetric allylic alkylation
Langlois, Jean-Baptiste,Alexakis, Alexandre
, p. 1877 - 1881 (2011/04/16)
Copper bottomed: The application of a previously described process of dynamic kinetic asymmetric transformation to acyclic substrates allowed the identification of a relevant kinetic process in the title reaction (see scheme; CuTC= copper(I) thiophencarboxylate, Naphth= naphthyl). The optimization of the reaction conditions and generality of the method, as well as mechanistic considerations are disclosed.
Generation and reactions of oxiranyllithiums by use of a flow microreactor system
Nagaki, Aiichiro,Takizawa, Eiji,Yoshida, Jun-Ichi
supporting information; experimental part, p. 14149 - 14158 (2011/02/25)
A flow microreactor system consisting of micromixers and microtubes provides an effective reactor for the generation and reactions of aryloxiranyllithiums without decomposition by virtue of short residence time and efficient temperature control. The depro
Direct copper-free domino conjugate addition-cycloallylation using organozinc reagents
Komanduri, Venukrishnan,Pedraza, Fernando,Krische, Michael J.
supporting information; experimental part, p. 1569 - 1576 (2009/07/30)
The Direct Approach: Enones possessing appendant allylic carbonates react directly with diorganozinc reagents in the presence of zinc diiodide [ZnI 2] to provide 5- and 6-membered ring products of tandem or domino conjugate addition-cycloallylation in good to excellent yield. In a related copper-free transformation, allylic carbonates are found to engage in direct allylic substitution with diorganozinc reagents.
Iron-catalyzed alkylation of alkenyl grignard reagents
Cahiez, Gerard,Duplais, Christophe,Moyeux, Alban
, p. 3253 - 3254 (2008/02/12)
The first iron-catalyzed cross-coupling reaction between alkenyl Grignard reagents and n- or s-alkyl bromides is described. The reaction is stereoselective and takes place in the presence of 5 mol % of [Fe(acac) 3MEDA/HMTA] (1:2:1) under very mild conditions (THF, 0°C, 45 min).
Understanding the effect of allylic methyls in olefin cross-metathesis
Courchay, Florence C.,Baughman, Travis W.,Wagener, Kenneth B.
, p. 585 - 594 (2007/10/03)
A series of NMR spectroscopy experiments have been conducted with both the model compound, 3-methyl-1-pentene and the corresponding ADMET monomer 3,6,9-trimethylundeca-1,10-diene (11) to better understand the effect of allylic methyls during olefin metath
