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A simple and efficient domino protocol has been developed for the preparation of biologically important benzamides, 2,2‐diazidobenzofuran‐3(2H)‐ones and benzoxazolones from various structurally and electronically divergent acetophenones and ortho‐hydroxyacetophenones in the presence of molecular iodine, sodium azide and sodium bicarbonate at 100 °C in good to excellent yields.
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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.
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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.
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Naganaboina Naveen Srinivasa Rao Koppolu Rengarajan Balamurugan 《Advanced Synthesis \u0026amp; Catalysis》2015,357(7):1463-1473
A practically simple and direct α‐alkylation of unactivated ketones using benzylic alcohols has been achieved. The in situ formed acetals are the key for the success of the reaction. The catalyst, silver hexafluoroantimonate(V) (AgSbF6) provides double activation by converting the ketone into an enol ether via acetal and generation of carbocationic center at the benzylic position of the benzylic alcohol. The alcohols include benzylic propargyl alcohols, cinnamyl alcohols, and diarylmethanols.
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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.
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Ryo Watari Yoshihito Kayaki Shin‐ichi Hirano Norio Matsumoto Takao Ikariya 《Advanced Synthesis \u0026amp; Catalysis》2015,357(7):1369-1373
Hydrogenation of carbon dioxide to formate was achieved using copper (Cu) catalysts in the presence of strong organic bases including amidines and guanidines. Specifically, 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) proved to be effective for the transformation of a 1:1 mixture of hydrogen and carbon dioxide into its formate salt under increased pressure in the presence of various Cu(I) and Cu(II) salts at 100 °C. A novel complex derived from copper iodide and DBU equally promoted the same reaction, indicating that DBU–Cu species are involved as real catalysts in this hydrogenation.
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Guangni Ding Chengjun Li Yifan Shen Bin Lu Zhaoguo Zhang Xiaomin Xie 《Advanced Synthesis \u0026amp; Catalysis》2016,358(8):1241-1250
Potassium hydroxide‐catalyzed hydrosilylation exhibits excellent activity and chemoselectivity for the reduction of cyclic imides under mild reaction conditions. The chemoselectivity of the reduction system may be readily tuned by changing the identity and stoichiometry of the hydrosilanes: a polymethylhydrosiloxane (PMHS)/potassium hydroxide reduction system resulted in the reduction of various cyclic imides to the corresponding ω‐hydroxylactams in 70–94% yield, while the diphenylsilane (Ph2SiH2)/potassium hydroxide reduction system selectively afforded the aryl lactams in 33–95% yield. These catalytic protocols tolerate diverse functional groups and are easy to scale up.
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Gang Zheng Xiaoli Ma Bangyu Liu Ying Dong Mang Wang 《Advanced Synthesis \u0026amp; Catalysis》2014,356(4):743-748
A metal‐free vinylic carbon‐hydrogen bond thiolation has been developed. Under the catalysis of iodine (10 mol%), the cyclization of α‐alkenoyl ketene dithioacetals afforded a broad range of polyfunctionalized 2‐methylene‐3‐thiophenones in good selectivity with moderate to excellent yields via tandem iodocyclization and dehydroiodination. The synthetic strategy can also be extended to the cyclization of ortho‐methylthiophenyl vinyl ketones leading to 2‐methylene‐3‐benzothiophenones.
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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.
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Qinquan Hu Yi Liu Xiaocong Deng Yanjun Li Yunfeng Chen 《Advanced Synthesis \u0026amp; Catalysis》2016,358(10):1689-1693
An aluminium(III) chloride‐catalyzed three‐component reaction of aromatic aldehydes, nitroalkanes, and sodium azide has been developed; this reaction sequence can be applied to a broad substrate scope and affords the corresponding 4‐aryl‐NH‐1,2,3‐triazoles in good to excellent yields. The milder reaction conditions and easier operation make this AlCl3‐catalyzed protocol more advantageous for the synthesis of 4‐aryl‐NH‐1,2,3‐triazoles.
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Ye‐Xiang Xie Ren‐Jie Song Yu Liu Yan‐Yun Liu Jian‐Nan Xiang Jin‐Heng Li 《Advanced Synthesis \u0026amp; Catalysis》2013,355(17):3387-3390
An efficient copper‐catalyzed α‐aminoxylation of ketones with 2,2,6,6‐tetramethylpiperidine‐1‐oxyl (TEMPO) is presented for the synthesis of 2‐aryloxy‐1‐aryl‐2‐(2,2,6,6‐tetramethylpiperidin‐1‐yloxy)ethanones in moderate to excellent yields. It is noteworthy that the copper/iron (Cu/Fe) catalyst can be recovered and reused several times with high catalytic reactivity.
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Ming‐Hua Zhuo Guo‐Feng Liu Shan‐Liang Song Dong An Jigang Gao Liangyu Zheng Suoqin Zhang 《Advanced Synthesis \u0026amp; Catalysis》2016,358(5):808-815
The first enantioselective Friedel–Crafts alkylation of indoles and pyrroles with 3‐hydroxy‐3‐indolyloxindoles to access two novel types of 3,3‐diaryloxindoles catalyzed by chiral imidodiphosphoric acids has been reported. A range of quaternary carbon centered 3,3‐diaryloxindoles were synthesized in high yield (up to >99%) with excellent enantioselectivity (up to 98% ee) at low catalyst loadings (as low as 0.5 mol%). The Friedel–Crafts reaction between indoles and 3‐hydroxy‐3‐indolyloxindoles is amenable to gram scale syntheses.