41010-17-7Relevant academic research and scientific papers
1,3-Oxyalkynylation of Aryl Cyclopropanes with Ethylnylbenziodoxolones Using Photoredox Catalysis
Studer, Armido,Zuo, Zhijun
supporting information, p. 949 - 954 (2022/02/07)
Alkynes and cyclopropanes are vital motifs in chemistry. Herein, a photoredox catalyzed 1,3-oxyalkynylation of aryl cyclopropanes with ethylnylbenziodoxolones (EBXs) in an atom-economic fashion is described. This cascade comprises single-electron oxidatio
Cooperative NHC/Photoredox Catalyzed Ring-Opening of Aryl Cyclopropanes to 1-Aroyloxylated-3-Acylated Alkanes
Daniliuc, Constantin G.,Studer, Armido,Zuo, Zhijun
supporting information, p. 25252 - 25257 (2021/10/29)
Cyclopropanes are an important class of building blocks in organic synthesis. Herein, a ring-opening/arylcarboxylation/acylation cascade reaction for the 1,3-difunctionalization of aryl cyclopropanes enabled by cooperative NHC and organophotoredox catalysis is reported. The cascade works on monosubstituted cyclopropanes that are in contrast to the heavily investigated donor–acceptor cyclopropanes more challenging to be difunctionalized. The key step is a radical/radical cross coupling of a benzylic radical generated in the photoredox catalysis cycle with a ketyl radical from the NHC catalysis cycle. The transformation features metal-free reaction conditions and tolerates a diverse range of functionalities.
Silylium-Ion-Promoted Ring-Opening Hydrosilylation and Disilylation of Unactivated Cyclopropanes
Bonetti, Vittorio,Klare, Hendrik F. T.,Oestreich, Martin,Roy, Avijit,Wang, Guoqiang,Wu, Qian
supporting information, (2020/02/04)
A silylium-ion-promoted ring-opening hydrosilylation of unactivated cyclopropanes is reported. The reaction is facilitated by the γ-silicon effect, and the regioselectivity is influenced by various stabilizing effects on the carbenium-ion intermediates, including the β-silicon effect. The experimental observations are in accord with the computed reaction mechanism. The work also showcases the ability of silylium ions to isomerize cyclopropyl to allyl groups, and the resulting α-olefins engage in a silylium-ion-mediated disilylation with hexamethyldisilane.
Suzuki coupling of cyclopropylboronic acid with aryl halides catalyzed by a palladium-tetraphosphine complex
Lemhadri, Mhamed,Doucet, Henri,Santelli, Maurice
, p. 121 - 128 (2007/10/03)
The tetraphosphine all-cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)- cyclopentane (Tedicyp) in combination with [Pd(C3H 5)Cl]2 affords a very efficient catalyst for the coupling of cyclopropylboronic acid with aryl bromides and aryl chlorides. Higher reactions rates were observed with aryl bromides than with aryl chlorides; however, even in the presence of 1-0.4% of catalyst, a few aryl chlorides gave the coupling products in good yields. A wide variety of substituents such as alkyl, methoxy, trifluoromethyl, acetyl, benzoyl, formyl, carboxylate, nitro, and nitrile on the aryl halides are tolerated. The coupling reaction of sterically very congested aryl bromides such as bromomesitylene or 2,4,6-triisopropylbromobenzene also proceeds in good yields. Copyright Taylor & Francis LLC.
Processing of cyclopropylarenes by toluene dioxygenase: Isolation and absolute configuration of metabolites
Finn, Kevin J.,Rochon, Lena,Hudlicky, Tomas
, p. 3606 - 3613 (2007/10/03)
Several arenes possessing a cyclopropyl substituent were subjected to enzymatic oxidation with toluene dioxygenase. The absolute configuration of metabolites was established by chemical means.
