- Silver-Mediated anti-Markovnikov and Markovnikov-Selective Hydrotrifluoromethylthiolation of Terminal Alkynes
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The first example of direct hydrotrifluoromethylthiolation of terminal alkynes in the presence of AgSCF3 and K2S2O8 was established for the synthesis of a variety of vinyl trifluoromethyl thioethers. The anti-Markovnikov and Markovnikov adducts were obtained in moderate to good yields via two different reaction systems. Studies to probe the mechanism of the anti-Markovnikov addition reactions including the radical trapping experiments, kinetic isotope effect experiments, and deuterated experiments for determination of H-sources were conducted.
- Wu, Wei,Dai, Wenpeng,Ji, Xinfei,Cao, Song
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- Radical Carbonyl Propargylation by Dual Catalysis
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Carbonyl propargylation has been established as a valuable tool in the realm of carbon–carbon bond forming reactions. The 1,3-enyne moiety has been recognized as an alternative pronucleophile in the above transformation through an ionic mechanism. Herein, we report for the first time, the radical carbonyl propargylation through dual chromium/photoredox catalysis. A library of valuable homopropargylic alcohols bearing all-carbon quaternary centers could be obtained by a catalytic radical three-component coupling of 1,3-enynes, aldehydes and suitable radical precursors (41 examples). This redox-neutral multi-component reaction occurs under very mild conditions and shows high functional group tolerance. Remarkably, bench-stable, non-toxic, and inexpensive CrCl3 could be employed as a chromium source. Preliminary mechanistic investigations suggest a radical-polar crossover mechanism, which offers a complementary and novel approach towards the preparation of valuable synthetic architectures from simple chemicals.
- Huang, Huan-Ming,Bellotti, Peter,Daniliuc, Constantin G.,Glorius, Frank
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supporting information
p. 2464 - 2471
(2020/12/07)
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- 7-Chloroquinolinotriazoles: Synthesis by the azide-alkyne cycloaddition click chemistry, antimalarial activity, cytotoxicity and SAR studies
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Twenty-seven 7-chloroquinolinotriazole derivatives with different substituents in the triazole moiety were synthesized via copper-catalyzed cycloaddition (CuAAC) click chemistry between 4-azido-7-chloroquinoline and several alkynes. All the synthetic compounds were evaluated for their in vitro activity against Plasmodium falciparum (W2) and cytotoxicity to Hep G2A16 cells. All the products disclosed low cytotoxicity (CC50 > 100 μM) and five of them have shown moderate antimalarial activity (IC50 from 9.6 to 40.9 μM). As chloroquine analogs it was expected that these compounds might inhibit the heme polymerization and SAR studies were performed aiming to explain their antimalarial profile. New structural variations can be designed on the basis of the results obtained.
- Pereira, Guilherme R.,Brand?o, Geraldo Célio,Arantes, Lucas M.,De Oliveira Jr., Háliton A.,De Paula, Renata Cristina,Do Nascimento, Maria Fernanda A.,Dos Santos, Fábio M.,Da Rocha, Ramon K.,Lopes, Júlio César D.,De Oliveira, Alaíde Braga
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p. 295 - 309
(2014/02/14)
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