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1.
Feihua Luo Jun Yang Zhengkai Li Haifeng Xiang Xiangge Zhou 《Advanced Synthesis \u0026amp; Catalysis》2016,358(6):887-893
A palladium(II)‐catalyzed direct arylation of methylene C(sp3) H bonds by 2‐methyl‐7‐aminobenzoxazole as an effective auxiliary is reported. This process exhibited high beta‐site selectivity, broad substrate scope, and compatibility with different functional groups with moderate to high yields up to 89%.
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A sequential one‐pot synthesis of Michael adducts of aroylmethylidenemalonates with activated aromatics is described. The method involves treatment of trans‐2‐aryl‐3‐nitro‐cyclopropane‐1,1‐dicarboxylates with boron trifluoride etherate to form aroylmethylidenemalonates in situ and then addition of activated aromatics such as indoles, carbazole, pyrrole, thiophenes, methoxybenzenes and benzodioxole followed by a catalytic amount of indium(III) triflate to the same reaction vessel. To prove the synthetic potential of the resulting Michael adducts, one of the adducts was transformed into a pharmaceutically interesting dihydropyridazinone derivative.
3.
Grard Cahiez Alban Moyeux Janine Cossy 《Advanced Synthesis \u0026amp; Catalysis》2015,357(9):1983-1989
Grignard reagents are probably the best organometallics to develop large‐scale eco‐friendly cross‐couplings compatible with the requirements of sustainable development. This account aims to highlight some reactions having an interesting industrial potential and gives the personal point of view of the authors on some attractive fields of research in this area.
4.
Siva Senthil Kumar Boominathan Wan‐Ping Hu Gopal Chandru Senadi Jeh‐Jeng Wang 《Advanced Synthesis \u0026amp; Catalysis》2013,355(18):3570-3574
A novel method has been developed for the synthesis of 3‐pyrrolines from β‐ketopropargylamines via a 5‐endo‐dig carbocyclization. This transformation involves a silver‐catalyzed Conia‐ene type reaction tolerating broad substrate scope with good to excellent yields. Furthermore, this methodology has been extended for the construction of 2‐substituted pyrroles under base‐mediated conditions.
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Zhiyong Wu Chao Pi Xiuling Cui Jie Bai Yangjie Wu 《Advanced Synthesis \u0026amp; Catalysis》2013,355(10):1971-1976
An efficient and concise one‐pot strategy for the direct alkylation of quinoline N‐oxides via palladium‐catalyzed dual C H bonds activation has been developed. This methodology provides quinoline‐containing heterocyclic molecules in moderate to excellent yields.
7.
Xu‐Heng Yang Xuan‐Hui Ouyang Wen‐Ting Wei Ren‐Jie Song Jin‐Heng Li 《Advanced Synthesis \u0026amp; Catalysis》2015,357(6):1161-1166
A new method for the nitrative spirocyclization of alkynes is described. This method involves the oxidative difunctionalization of alkynes initiated by a radical attack pathway using t‐BuONO (tert‐butyl nitrite) combined with water as the nitro source and TEMPO [(2,2,6,6‐tetramethyl‐piperidin‐1‐yl)oxyl] as the initiator, and it represents a new example of oxidative alkyne difunctionalization via the formation of C N/C C bonds for the assembly of nitroalkene unit‐containing spirocycles.
8.
Krzysztof Kuciski Piotr Pawlu Grzegorz Hreczycho 《Advanced Synthesis \u0026amp; Catalysis》2015,357(18):3936-3942
Scandium(III) triflate promoted highly selective addition of thiols to functionalized olefins under mild conditions. The addition follows anti‐Markovnikov regioselectivities, which are unusual for Lewis acids‐catalyzed hydrothiolation. This reaction marks broad functional groups tolerance, which opens a beneficial synthetic route to functionalized and biologically active thio‐compounds. This method is broadly applicable and offers a simple work‐up in the green manner.
9.
Xiaolan Chen Xu Li Zhibo Qu Diandian Ke Lingbo Qu Likun Duan Wenpeng Mai Jinwei Yuan Jianyu Chen Yufen Zhao 《Advanced Synthesis \u0026amp; Catalysis》2014,356(9):1979-1985
A synthetic strategy has been developed for the synthesis of 2‐dialkylaminoquinolines from easily available quinoline N‐oxides, tertiary amines, diisopropyl H‐phosphonate and carbon tetrachloride (CCl4) in one pot under metal‐free conditions at room temperature.
10.
Youngtaek Moon Soonhyung Kwon Dahye Kang Honggu Im Sungwoo Hong 《Advanced Synthesis \u0026amp; Catalysis》2016,358(6):958-964
We have developed a new strategy for palladium‐catalyzed arylation reactions with triazolopyridines, wherein two different chemical transformations (C‐3 vs. C‐7) are observed by differentiating the substrates using different bases. The reactive palladium carbenoids were directly generated from triazolopyridines and underwent denitrogenative arylations with aryl bromides. Intriguingly, when potassium carbonate was replaced with potassium tert‐butoxide, direct C H arylation occurred at the most acidic position (C‐7). Moreover, two different catalytic arylation events were successfully performed in a one‐pot sequence, providing a convenient access to 6‐aryl‐2‐α‐styrylpyridines.
11.
Jun Xu Nandini Sharma Upendra K. Sharma Zhenghua Li Gonghua Song Erik V. VanderEycken 《Advanced Synthesis \u0026amp; Catalysis》2015,357(12):2615-2621
A pentamethylcyclopentadienylrhodium(III)‐catalyzed regioselective synthesis of indole‐2‐carboxamides is described employing N‐pyrimidylindoles and isocyanates as coupling partners via C H functionalization. A wide variety of indole‐2‐carboxamides can be synthesized via this method under relatively mild conditions with broad functional group tolerance. The effect of various directing group on this transformation was also studied, unveiling the pyrimidyl group as an easily installable and removable directing group.
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Shiguang Pan Naoto Ryu Takanori Shibata 《Advanced Synthesis \u0026amp; Catalysis》2014,356(5):929-933
A cationic iridium‐catalyzed C‐7 alkylation of N‐substituted indoline derivatives with various alkenes has been developed. A variety of 7‐alkylindolines were obtained in moderate to high yields. This protocol relies on the use of the carbonyl group on the nitrogen atom of indoline as a directing group and it is potentially applicable to the large‐scale synthesis of 7‐alkylindoles.
14.
Fleur Drouet Jieping Zhu Graldine Masson 《Advanced Synthesis \u0026amp; Catalysis》2013,355(18):3563-3569
The iron(III) chloride‐multicatalyzed dioxygenation of enamides with TEMPO in the presence of alcohols has been developed. This multicomponent domino process affords efficient new strategies for the synthesis of α‐oxy‐N‐acylhemiaminals or α‐oxyimides in good to excellent yields under mild conditions.
15.
Farnaz Jafarpour Hamideh Hazrati Masoumeh Darvishmolla 《Advanced Synthesis \u0026amp; Catalysis》2014,356(18):3784-3788
An efficient regioselective synthesis of 2‐acylpyrroles via palladium‐catalyzed addition of pyrroles with benzonitriles and subsequent hydrolysis is developed. The direct acylation reaction of protected as well as (NH)‐free pyrroles proceeded smoothly to afford 2‐acylpyrrole scaffolds of high biological interest.
16.
Christine M. M. Hendriks Rebekka A. Bohmann Marina Bohlem Carsten Bolm 《Advanced Synthesis \u0026amp; Catalysis》2014,356(8):1847-1852
A general method for the N‐alkylation of NH‐sulfoximines and NH‐sulfondiimines has been developed, employing alkyl bromides with KOH in DMSO at room temperature. A variety of previously inaccessible N‐alkylated sulfoximines and sulfondiimines was prepared in good to excellent yields (up to 97%). As an application, the conditions were used to access the biologically active Suloxifen.
17.
Alexander W. Jones Marie‐Laure Louillat‐Habermeyer Frederic W. Patureau 《Advanced Synthesis \u0026amp; Catalysis》2015,357(5):945-949
What does it take to force a rigid and strained dehydrogenative ring closure, for example, in phenylcarbazoles? Since the works of Buchwald and Fagnou, palladium‐catalysed ring‐closing dehydrogenative reactions are legion, but will not operate when the strain at the reductive elimination stage becomes too large. We propose here a “muscled up” super‐oxidative palldium‐catalysed C H activation method for the ring closure of strained phenylcarbazoles.
18.
Hong‐Wu Zhao Hai‐Liang Pang Ting Tian Bo Li Xiao‐Qin Chen Xiu‐Qing Song Wei Meng Zhao Yang Yue‐Yang Liu Yu‐Di Zhao 《Advanced Synthesis \u0026amp; Catalysis》2016,358(11):1826-1832
In the presence of sodium carbonate, the [4+3] cycloadditions of α‐halogeno hydrazones with nitrones were performed efficiently, and affording 2,3,4,7‐tetrahydro‐1,2,4,5‐oxatriazepines in moderate to high yields.
19.
Yinghua Yu Lei Zhu Yun Liao Zhifeng Mao Xueliang Huang 《Advanced Synthesis \u0026amp; Catalysis》2016,358(7):1059-1064
The skeletal rearrangement of ether tethered N‐sulfonyl‐1,2,3‐triazoles has been achieved by rhodium(II) catalysis. This method offers a rapid entry to 2‐aminoindanone and dihydroisoquinoline architectures which can be further transformed to other valuable building blocks, such as vicinal aminoindanols, isoquinolines and isoquinolinones. A pathway involving an azavinyl rhodium carbene intermediate was proposed according to a preliminary mechanistic study.
20.
Zhenguang Zhao Tao Wang Lin Yuan Xu Hu Fei Xiong Junfeng Zhao 《Advanced Synthesis \u0026amp; Catalysis》2015,357(11):2566-2570
A direct oxidative amidation between methylarenes and aqueous ammonia using a tert‐butyl hydroperoxide and tetrabutylammonium iodide (TBHP/TBAI) oxidation system with co‐catalysis of iron(III) chloride has been developed. Both coupling partners were used in their native form to render prior functionalization unnecessary and afford a facile approach to aromatic primary amides.