10292-66-7Relevant academic research and scientific papers
Aryl and vinyl cyclopropanes through the in situ generation of B- cyclopropyl-9-BBN and its Suzuki-Miyaura coupling
Soderquist, John A.,Huertas, Ramon,Leon-Colon, Gisela
, p. 4251 - 4255 (2000)
Dihydroboration of propargyl bromide with 9-BBN-H followed by treatment of the adduct with aqueous sodium hydroxide affords the hydroxy(cycloropropyl)borate complex (1), which undergoes efficient palladium-catalyzed cross-coupling to produce a variety of aryl and vinyl cyclopropanes (2) in good to excellent yields. (C) Elsevier Science Ltd.
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.
Reductive Cyclopropanations Catalyzed by Dinuclear Nickel Complexes
Zhou, You-Yun,Uyeda, Christopher
supporting information, p. 3171 - 3175 (2016/03/12)
Dinuclear Ni complexes supported by naphthyridine-diimine (NDI) ligands catalyze the reductive cyclopropanation of alkenes with CH2Cl2 as the methylene source. The use of mild terminal reductants (Zn or Et2Zn) confers significant functional-group tolerance, and the catalyst accommodates structurally and electronically diverse alkenes. Mononickel catalysts bearing related N chelates afford comparatively low cyclopropane yields (≤20 %). These results constitute an entry into catalytic carbene transformations from oxidized methylene precursors.
Iron-catalyzed cyclopropanation in 6 M KOH with in situ generation of diazomethane
Morandi, Bill,Carreira, Erick M.
scheme or table, p. 1471 - 1474 (2012/07/13)
Diazomethane is a common and versatile reagent in organic synthesis whose broader use is generally impeded by its explosiveness and toxicity. Here we report that a simple iron porphyrin complex catalyzes the cyclopropanation of styrenes, enynes, and dienes under the demanding conditions [aqueous 6 molar potassium hydroxide (KOH) solution, open to air] necessary for the in situ generation of diazomethane from a water-soluble diazald derivative. A biphasic reaction medium arising from the immiscibility of the olefin substrates with water appears essential to the overall efficiency of the process. The work we describe highlights an approach to catalysis with untoward reactive intermediates, in which the conditions for their generation under operationally safe regimes dictate catalyst selection.
Cross-coupling of mesylated phenol derivatives with potassium cyclopropyltrifluoroborate
Molander, Gary A.,Beaumard, Floriane,Niethamer, Terren K.
experimental part, p. 8126 - 8130 (2011/11/12)
C-O activation of mesylates by a palladium catalyst and subsequent cross-coupling with potassium cyclopropyltrifluoroborate have been achieved with high yield. Both electron-enriched and electron-deficient aryl mesylates are suitable electrophilic partners for the Suzuki-Miyaura reaction. The scope was successfully extended to heteroaryl mesylates with yields up to 94%. (Figure presented)
A general and special catalyst for suzuki-miyaura coupling processes
Tang, Wenjun,Capacci, Andrew G.,Wei, Xudong,Li, Wenjie,White, Andre,Patel, Nitinchandra D.,Savoie, Jolaine,Gao, Joe J.,Rodriguez, Sonia,Qu, Bo,Haddad, Nizar,Lu, Bruce Z.,Krishnamurthy, Dhileepkumar,Yee, Nathan K.,Senanayake, Chris H.
supporting information; experimental part, p. 5879 - 5883 (2010/10/01)
(Figure Presented) Biaryl monophosphorus ligands containing a 2,3-dihydrobenzo[d][1,3]oxaphosphole framework are highly effective for the palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of a wide range of substrates. Ligand 1 has demonstrated excellent performance for coupling reactions of extremely hindered arylboronic acids.
Cross-coupling of cyclopropyl- and cyclobutyltrifluoroborates with aryl and heteroaryl chlorides
Molander, Gary A.,Gormisky, Paul E.
, p. 7481 - 7485 (2008/12/23)
(Chemical Equation Presented) Suitable conditions were found for the Suzuki-Miyaura cross-coupling reaction of potassium cyclopropyl-and cyclobutyltrifluoroborates with aryl chlorides. Both of these secondary alkyl trifluoroborates coupled in moderate to excellent yield with electron-rich, electron-poor, and hindered aryl chlorides to give a variety of substituted aryl cyclopropanes and cyclobutanes.
Novel photohydration of non-conjugated aryl/olefin bichromophores within cyclodextrin cavities
Benali,Jimenez,Miranda,Tormos
, p. 2328 - 2329 (2007/10/03)
Cyclodextrin media are used to achieve photochemical water addition to isolated, acyclic double bonds via intramolecular interaction with excited arenes.
