22219-36-9Relevant academic research and scientific papers
Synthesis of Quinolines via the Metal-free Visible-Light-Mediated Radical Azidation of Cyclopropenes
Smyrnov, Vladyslav,Muriel, Bastian,Waser, Jerome
, p. 5435 - 5439 (2021/07/21)
We report the synthesis of quinolines using cyclopropenes and an azidobenziodazolone (ABZ) hypervalent iodine reagent as an azide radical source under visible-light irradiation. Multisubstituted quinoline products were obtained in 34-81% yield. The reaction was most efficient for 3-trifluoromethylcyclopropenes, affording valuable 4-trifluoromethylquinolines. The transformation probably proceeds through the cyclization of an iminyl radical formed by the addition of the azide radical on the cyclopropene double bond, followed by ring-opening and fragmentation.
Photoredox-Catalyzed α-Aminoalkylcarboxylation of Allenes with CO2
Hahm, Hyungwoo,Baek, Doohyun,Kim, Dowon,Park, Seongwook,Ryoo, Jeong Yup,Hong, Sukwon
supporting information, p. 3879 - 3884 (2021/05/29)
The photoredox-catalyzed α-aminoalkylcarboxylation of aryl allenes with CO2 and N,N-dimethylanilines is reported for the first time (26 examples, up to 96% yield). In the case of electron-deficient allenes, good regioselectivity was observed (up to 94:6), exclusively generating kinetic products over thermodynamic products. This protocol is a novel synthetic method for highly functionalized β,γ-unsaturated γ-aminobutyric esters.
Regioselective Diboron-Mediated Semireduction of Terminal Allenes
Gates, Ashley M.,Santos, Webster L.
, p. 4619 - 4624 (2019/12/11)
A method for the regioselective reduction of the terminal double bond of 1,1-disubstituted allenes has been developed. In the presence of a palladium catalyst, tetrahydroxydiboron and stoichiometric water, allene semireduction proceeds in high yield to afford Z-alkenes selectively.
Rhodium-catalyzed polymerization of 3,3-diarylcyclopropenes involving a 1,4-rhodium migration
Shintani, Ryo,Iino, Ryo,Nozaki, Kyoko
supporting information, p. 7849 - 7852 (2014/06/23)
A new mode of metal-catalyzed polymerization reaction has been developed by exploiting the ability of 1,4-rhodium migration of an organorhodium(I) species. Specifically, it has been demonstrated that 3,3-diarylcyclopropenes undergo polymerization through
Reactions of vinylidenecyclopropanes with diphenyl diselenide in the presence of AIBN and thermally-induced further transformations
Yuan, Wei,Wei, Yin,Shi, Min,Li, Yuxue
supporting information; scheme or table, p. 1280 - 1285 (2012/03/26)
In conclusion, we have developed a novel tandem reaction of VDCPs 1 with PhSeSePh to give the corresponding bicyclo[3.1.0]hexane derivatives 4 in good yields in the presence of AIBN, which could undergo a thermal-induced radical 1,4-hydrogen shift through
An efficient method for the synthesis of alkylidenecyclobutanones by gold-catalyzed oxidative ring enlargement of vinylidenecyclopropanes
Yuan, Wei,Dong, Xiang,Wei, Yin,Shi, Min
, p. 10501 - 10505 (2012/11/13)
Rings of gold: Vinylidenecyclopropanes can undergo efficient oxidative ring enlargements under mild conditions to give the corresponding alkylidenecyclobutanone derivatives in good yields (see scheme). A plausible mechanism for this transformation has bee
Halogenation reagents initiating ring opening of vinylidenecyclopropanes: Easy access to halogenated tetrahydropyrans
Yuan, Wei,Shi, Min
supporting information; scheme or table, p. 995 - 999 (2011/06/17)
A novel synthetic protocol that uses halogenation reagents (NBS, NIS and selectfluor) to initiate intramolecular ring-opening reactions of diarylvinylidenecyclopropanes (VDCPs) connected to alcohol-bearing chains has been developed. The approach provides
Lewis acid promoted reactions of ethenetricarboxylates with allenes: Synthesis of indenes and γ-lactones via conjugate addition/cyclization reaction
Yamazaki, Shoko,Yamamoto, Yuko,Fukushima, Yugo,Takebayashi, Masachika,Ukai, Tetsuma,Mikata, Yuji
supporting information; experimental part, p. 5216 - 5222 (2010/09/05)
(Figure presented) Indenes are important core structures in organic chemistry. Few simple arylallenes have been used to construct indene skeletons by Friedel-Crafts reaction. Lewis acid catalyzed reaction of ethenetricarboxylates 1 and arylallenes has been examined in this study. The reaction of arylallenes and ethenetricarboxylate triesters with SnCl4 gave indene derivatives efficiently, via a conjugate addition/Friedel-Crafts cyclization reaction. On the other hand, the reactions of 1,1-diethyl 2-hydrogen ethenetricarboxylate and arylallenes or alkylallenes with SnCl4 at -78 °C or room temperature and subsequent treatment with Et3N gave γ-lactones. The reactions of triethyl ethenetricarboxylate and 1,1-dialkylallenes with SnCl4 at room temperature also gave γ-lactones.
Rhodium(I)-catalyzed intramolecular ene reaction of vinylidenecyclopropanes and alkenes for the formation of bicyclo[5.1.0]octylenes
Li, Wei,Yuan, Wei,Shi, Min,Hernandez, Erik,Li, Guigen
supporting information; scheme or table, p. 64 - 67 (2010/03/03)
"Chemical Equation Presented" An efficient catalytic system for the intramolecular ene reaction of allene and alkene of diarylvinylidenecyclopropanes has been established. The reaction was achieved by using [RhCl(CO)2]2 as the cataly
Au/Ag-catalyzed intramolecular ring-opening of vinylidene-cyclopropanes (VDCPs): An easy access to functional tetrahydropyrans
Li, Wel,Yuan, Wel,Pindl, Surech,Shi, Min,Li, Guigen
supporting information; experimental part, p. 920 - 923 (2010/06/16)
Chemical Equation Presentation An intramolecular ring-opening of vinylidenecyclopropanes (VDCPs) tethered with alcohol chains has been established. A serles of transition metal catalysts and their combinations have been screened under mild conditions, and
