- Synthesis of 7,7′-Dihydroxy-8,8′-biquinolyl (azaBINOL) via Pd-catalyzed directed double C-H functionalization of 8,8′-biquinolyl: Emergence of an atropos from a tropos state
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7,7′-Dihydroxy-8,8′-biquinolyl (azaBINOL) was prepared from 2-chloroaniline in four steps: (1) the Skraup reaction, (2) Ni-catalyzed reductive coupling of 8-chloroquinoline, (3) Pd(II)-catalyzed double C-H functionalization of 8,8′-biquinolyl mediated by
- Wang, Chao,Flanigan, Darrin M.,Zakharov, Lev N.,Blakemore, Paul R.
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- A general electrochemical strategy for the Sandmeyer reaction
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Herein we report a general electrochemical strategy for the Sandmeyer reaction. Using electricity as the driving force, this protocol employs a simple and inexpensive halogen source, such as NBS, CBrCl3, CH2I2, CCl4, LiCl and NaBr for the halogenation of aryl diazonium salts. In addition, we found that these electrochemical reactions could be performed using anilines as the starting material in a one-pot fashion. Furthermore, the practicality of this process was demonstrated in the multigram scale synthesis of aryl halides using highly inexpensive graphite as the electrode. A series of detailed mechanism studies have been performed, including radical clock and radical scavenger study, cyclic voltammetry analysis and in situ electron paramagnetic resonance (EPR) analysis.
- Liu, Qianyi,Sun, Beiqi,Liu, Zheng,Kao, Yi,Dong, Bo-Wei,Jiang, Shang-Da,Li, Feng,Liu, Guoquan,Yang, Yang,Mo, Fanyang
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- Relative Reactivities of Three Isomeric Aromatic Biradicals with a 1,4-Biradical Topology Are Controlled by Polar Effects
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Unexpectedly, the 5-dehydroquinoline radical cation was formed in the gas phase from the 5-iodo-8-nitroquinolinium cation upon ion-trap collision-activated dissociation. This reaction involves the cleavage of a nitro group to generate an intermediate monoradical, namely, the 8-dehydro-5-iodoquinolinium cation, followed by rearrangement through abstraction of a hydrogen atom from the protonated nitrogen atom by the radical site. Dissociation of the rearranged radical cation through elimination of an iodine atom generates the 5-dehydroquinoline radical cation. The mechanism was probed by studying isomeric biradicals and performing quantum chemical calculations. The 5-dehydroquinoline radical cation showed greater gas-phase reactivity toward dimethyl disulfide, cyclohexane, and allyl iodide than the isomeric 5,8-didehydroquinolinium cation, which is more reactive than the isomeric 5,8-didehydroisoquinolinium cation studied previously. All three isomers have a 1,4-biradical topology. The order of reactivity is rationalized by the vertical electron affinities of the radical sites of these biradicals instead of their widely differing singlet–triplet splittings.
- Ma, Xin,Jin, Chunfen,Wang, Duanda,Nash, John J.,Kentt?maa, Hilkka I.
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- Coordination complexes featuring bidentate κN, κI-8-iodoquinoline
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Coordination complexes featuring bidentate κN, κI-8-iodoquinoline were formed upon combination of metal salts (M = Cu+, Cu2+, Ag+, Pd2+, and Hg2+) and 8-iodoquinoline. Single crystal X-ray diffraction
- Dhungana, Pramod,Nandy, Pranab K.,Hussain, Anwar,Hoefelmeyer, James D.
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p. 3170 - 3181
(2022/01/19)
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- Generation of Organozinc Reagents by Nickel Diazadiene Complex Catalyzed Zinc Insertion into Aryl Sulfonates
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The generation of arylzinc reagents (ArZnX) by direct insertion of zinc into the C?X bond of ArX electrophiles has typically been restricted to iodides and bromides. The insertions of zinc dust into the C?O bonds of various aryl sulfonates (tosylates, mesylates, triflates, sulfamates), or into the C?X bonds of other moderate electrophiles (X=Cl, SMe) are catalyzed by a simple NiCl2–1,4-diazadiene catalyst system, in which 1,4-diazadiene (DAD) stands for diacetyl diimines, phenanthroline, bipyridine and related ligands. Catalytic zincation in DMF or NMP solution at room temperature now provides arylzinc sulfonates, which undergo typical catalytic cross-coupling or electrophilic substitution reactions.
- Klein, Philippe,Lechner, Vivien Denise,Schimmel, Tanja,Hintermann, Lukas
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supporting information
p. 176 - 180
(2019/12/11)
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- PHENANTHROLINONE DERIVATIVES FOR USE IN THE TREATMENT OF BACTERIAL INFECTIONS
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The present invention is in the field of therapeutic drugs to treat bacterial infections. In particular, the invention provides phenanthrolinone compounds for use in the treatment of bacterial infections, for example tuberculosis.
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Page/Page column 19
(2019/08/20)
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- Push-pull isomers of indolizino[6,5,4,3-: Def] phenanthridine decorated with a triarylboron moiety
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1,3-Dipolar cycloaddition reactions between a new azomethine ylide and three BPhMes2-functionalized internal alkynes produced three pairs of fluorescent push-pull regioisomers, which show distinct electronic and photophysical properties. All the six compounds are found to exhibit charge-transfer (CT) fluorescence, and some of which show rare and interesting temperature "turn-on" fluorescence.
- Dong, Lei,Saraci, Felix,Yuan, Kang,Wang, Xiang,Wang, Suning
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supporting information
p. 6170 - 6477
(2019/07/09)
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- From Anilines to Quinolines: Iodide- and Silver-Mediated Aerobic Double C?H Oxidative Annulation–Aromatization
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Quinoline synthesis from easily accessible raw materials such as anilines is a valuable and meaningful task. Herein, we communicate an iodide- and silver-mediated C?H/C?H oxidative annulation–aromatization between anilines and allyl alcohols. This protocol provides a direct route to the synthesis of quinoline derivatives from inexpensive commodities. Various kinds of anilines, even heterocyclic anilines, were shown to be workable substrates, generating the corresponding multi-substituted quinolines in good yields.
- Wu, Jiwei,Liao, Zhixiong,Liu, Dong,Chiang, Chien-Wei,Li, Zheng,Zhou, Zhonghao,Yi, Hong,Zhang, Xu,Deng, Zixin,Lei, Aiwen
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supporting information
p. 15874 - 15878
(2017/10/23)
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- One-pot synthesis of N-aryl propargylamine from aromatic boronic acid, aqueous ammonia, and propargyl bromide under microwave-assisted conditions
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A facile, one-pot synthesis of N-aryl propargylamine from aromatic boronic acid, aqueous ammonia, and propargyl bromide has been achieved under microwave-assisted conditions. The reactions can be smoothly completed within a total 10 min through a two-step procedure, including copper-catalyzed coupling of aromatic boronic acids with aqueous ammonia and following propargylation by propargyl bromide.
- Jiang, Yu-Bo,Zhang, Wen-Sheng,Cheng, Hui-Ling,Liu, Yu-Qi,Yang, Rui
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p. 779 - 782
(2014/06/09)
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- Copper-promoted reductive coupling of aryl iodides with 1,1,1-trifluoro-2-iodoethane
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An efficient Cu-promoted reductive coupling of aryl iodides with 1,1,1-trifluoro-2-iodoethane has been developed. This reaction could occur in good yields under milder conditions as compared with previous studies. The reaction tolerated nitro, formyl, ester, ether, carbonyl, sulfonyl, and even azo groups.
- Xu, Song,Chen, Huan-Huan,Dai, Jian-Jun,Xu, Hua-Jian
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supporting information
p. 2306 - 2309
(2014/05/20)
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