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1.
Rengwei Sun Wei Song Chunmei Ma Huiwen Zhang Xinhong Yu 《Advanced Synthesis \u0026amp; Catalysis》2016,358(24):3977-3982
A direct access to multisubstituted 1,3‐dienes by α‐exclusive alkylidenation of crotonic derivatives has been developed. This protocol, mediated by titanium tetrachloride chelation, features excellent regio‐ and stereoselectivity, mild reaction conditions, easy operation and wide substrate scope. Conversions of the derived dienes to other useful molecules were also explored.
2.
Feifei Li Cong Shen Jian Zhang Ling Wu Xupeng Zhuo Liyuan Ding Guofu Zhong 《Advanced Synthesis \u0026amp; Catalysis》2016,358(24):3932-3937
An inexpensive ruthenium‐catalyzed direct C–H olefination of aromatic carboxamides with allyl acetate was developed. This external oxidant‐free protocol provided an efficient route for the synthesis of useful trans‐styrene derivatives in high to excellent yields. The olefination reaction exhibited excellent regioselectivities and allowed the presence of a wide range of functional groups, such as OMe, F, Cl, Br, I, CF3, NMe2, as well as NO2.
3.
Tenglong Guo Quanbin Jiang Zhengkun Yu 《Advanced Synthesis \u0026amp; Catalysis》2016,358(21):3450-3457
A copper(I)‐catalyzed, (diacetoxyiodo)benzene [PhI(OAc)2]‐mediated ring‐expansion/thiolactonization of α‐oxo ketene dithioacetals was efficiently realized via azidation of the internal olefinic C−H bond with sodium azide under mild conditions. Sequential amination, ring‐expansion rearrangement, and thiolactonization occurred to form aminated thiolactones in the presence of acetic anhydride as the additive, while only C−H amination to afford the unprotected enamines occurred when using ammonium sulfide as a reducing additive. The in situ generated vinyl azides were confirmed as the reactive intermediates, which were captured by phenylacetylene to produce triazoles. This protocol provides a concise route to thiolactone derivatives and unprotected enamines.
4.
Hongxiang Wu Yue Li Ming Cui Junsheng Jian Zhuo Zeng 《Advanced Synthesis \u0026amp; Catalysis》2016,358(23):3876-3880
A palladium‐catalyzed cross‐coupling of activated amides with arylboronic acids has been developed via C–N bond cleavage. This approach demonstrated high tolerance to a variety of alkyl, aryl, heterocyclic and vinyl substituents. Unsymmetrical ketones could be achieved in excellent yield under mild conditions with 1% catalyst loadings.
5.
Sreekumar Pankajakshan Wei Li Ang Sivarampanicker Sreejith Mihaiela Corina Stuparu Teck‐Peng Loh 《Advanced Synthesis \u0026amp; Catalysis》2016,358(19):3034-3038
N‐Alkenylated triazolinone ylides were generated through copper‐catalyzed oxy‐N‐alkenylation of triazolopyridines. The mechanistic course of this aerobic tandem reaction has been experimentally elucidated and primary photophysical data of the ylide products are also given.
6.
Yun Wu Hao‐Ran Zhang Ruo‐Xing Jin Quan Lan Xi‐Sheng Wang 《Advanced Synthesis \u0026amp; Catalysis》2016,358(22):3528-3533
The first example of a nickel‐catalyzed C–H trifluoromethylation of electron‐rich heteroarenes, including imidazopyridines, indoles and thiophenes, has been developed with the commercially available and relatively inexpensive industrial raw material iodotrifluoromethane (CF3I) as the trifluoromethylating reagent. The synthetic potential of this method is demonstrated by its successful application to the direct trifluoromethylation of the biologically active molecules melatonin and zolmitriptan.
7.
Fuhong Xiao Shuqing Chen Cheng Li Huawen Huang Guo‐Jun Deng 《Advanced Synthesis \u0026amp; Catalysis》2016,358(23):3881-3886
A copper‐catalyzed three‐component (arenes, iodohydrocarbon, and sulfur powder) synthesis of substituted aryl sulfides has been developed. Water is used as the green solvent in a simple and environmentally friendly procedure. Various functional groups attached to the substrates were well tolerated in this process to afford the corresponding products in moderate to good yields.
8.
Xiaoxu Yang Xiqing Jin Congyang Wang 《Advanced Synthesis \u0026amp; Catalysis》2016,358(15):2436-2442
So far, the direct C−H alkenylation of aromatic nitriles with alkynes has not been achieved. Herein, we discribe the first manganese‐catalyzed C−H alkenylation of aromatic N−H imidates to access mono‐alkenylated aromatic nitriles. The reaction is accelerated by the presence of a catalytic amount of sodium pivalate. This protocol is also highlighted by the simple catalytic system, good compatibility of functional groups, and excellent mono‐/dialkenylation selectivity as well as E/Z stereoselectivity.
9.
Xiying Zhang Jianlin Zhang Lili Lin Haifeng Zheng Wangbin Wu Xiaohua Liu Xiaoming Feng 《Advanced Synthesis \u0026amp; Catalysis》2016,358(19):3021-3026
A highly efficient chiral N,N′‐dioxide‐zinc(II) complex catalytic system has been developed for the enantioselective aza‐Friedel–Crafts reaction of isatin‐derived ketimines with indoles. A series of enantiomerically enriched 3‐indolyl‐3‐aminooxindoles containing a tetrasubstituted stereocenter were obtained in up to 99% yield with up to 96% ee. Furthermore, control experiments provide a fundamental sight into the mechanism of the reaction.
10.
Rajnikanth Sunke E. V. Venkat Shivaji Ramarao Suresh Babu Nallapati Raghavender Medisetti Pushkar Kulkarni Ravi Kumar Kapavarapu Ramudu Bankala Kishore V. L. Parsa Manojit Pal 《Advanced Synthesis \u0026amp; Catalysis》2016,358(20):3201-3205
A copper‐catalyzed new domino reaction allowed the facile and direct construction of the dibenzo‐fused azepinone ring leading to an array of novel small molecules. The co‐catalyst, ligand or additive free one‐pot method afforded a unique class of functionalized derivatives, one of which showed encouraging PDE4 inhibition in vitro and apoptosis in vivo.
11.
Longyang Dian Hui Zhao Daisy Zhang‐Negrerie Yunfei Du 《Advanced Synthesis \u0026amp; Catalysis》2016,358(15):2422-2426
A cobalt‐catalyzed regioselective C‐3 alkylation of coumarins was realized under mild reaction conditions, during which a variety of substituted coumarins including those containing sensitive functional groups could smoothly undergo the selective C(sp2)−C(sp3) bond formation with a series of cyclic or straight‐chain alkyl ethers.
12.
By combining an organocatalyzed Michael addition of 1,3‐diketones to hydroxy‐nitroolefins with a subsequent, innovative iron(0)‐catalyzed fragmentation, key enantioenriched ketones possessing additional nitro and protected alcohol functions could efficiently be prepared under excellent enantiocontrol (typically 95% ee). The reaction was made possible by the discovery that photochemical activation of iron pentacarbonyl [Fe(CO)5], a cheap widely available complex, efficiently catalyzed a Claisen‐type fragmentation under mild conditions, avoiding decomposition of the intermediates and products.
13.
Suresh Babu Nallapati Bagineni Prasad B. Yogi Sreenivas Rajnikanth Sunke Y. Poornachandra C. Ganesh Kumar B. Sridhar S. Shivashankar K. Mukkanti Manojit Pal 《Advanced Synthesis \u0026amp; Catalysis》2016,358(21):3387-3393
The formation of an amide bond via incorporation of two isocyanide units during a palladium‐catalyzed construction of the indoloquinoline ring afforded N‐substituted 6H‐indolo[2,3‐b]quinoline‐11‐carboxamides as new cytotoxic agents. The solvent and base play a key role in the selective and unprecedented synthesis of this class of amides.
14.
Qiangqiang Yan Tangxin Xiao Zhanxiang Liu Yuhong Zhang 《Advanced Synthesis \u0026amp; Catalysis》2016,358(16):2707-2711
Cobalt‐catalyzed C−H amination of arenes with alkylamines by the assistance of 8‐aminoquinoline as auxiliary through sp2 C−H bond functionalization has been achieved. Attractive features of this protocol include the low loading of the cobalt catalyst and the readily available reagents.
15.
Wen‐Juan Shi Hong‐Wei Zhao Yang Wang Zhi‐Chao Cao Li‐Sheng Zhang Da‐Gang Yu Zhang‐Jie Shi 《Advanced Synthesis \u0026amp; Catalysis》2016,358(15):2410-2416
Aryl carbamates were for the first time applied as electrophiles in the cross‐coupling with arylsilanes via nickel or iron catalysis to construct valuable biaryl compounds. This new coupling reaction features a good group tolerance and non‐sensitivity to steric hindrance on both aryl carbamates and arylsilanes.
16.
Shuai‐Shuai Li Ying‐Qi Xia Chen‐Fei Liu Guo‐Tai Zhang Fu Su Xiao‐Mei Zhang Lin Dong 《Advanced Synthesis \u0026amp; Catalysis》2016,358(23):3724-3729
An efficient rhodium(III)‐catalyzed vinylic sp2 C–H bond activation of 7‐azaindoles with alkynes is reported, leading to the controlled synthesis of stereodefined diene and fused polycyclic heteroarene products. The novel strategy for the synthesis of diverse coupling products was controlled by the reaction conditions and the substitutions on the vinyl group.
17.
Rameshwar Prasad Pandit Sung Hong Kim Yong Rok Lee 《Advanced Synthesis \u0026amp; Catalysis》2016,358(22):3586-3599
A novel and facile iron‐catalyzed tandem annulation of o‐phenylenediamines and diazocarbonyls in water for the construction of polyfunctionalized quinoxalines has been developed. The key strategy includes the one‐pot domino N−H insertion, cyclization, and oxidation reactions. This protocol offers a safe and mild synthetic approach to access a variety of quinoxaline derivatives in high yields. This methodology also allows the formation of biologically interesting pyrazines and benzoquinoxalines.
18.
Mamoru Tobisu Jiangning Zhao Hirotaka Kinuta Takayuki Furukawa Takuya Igarashi Naoto Chatani 《Advanced Synthesis \u0026amp; Catalysis》2016,358(15):2417-2421
The nickel‐catalyzed borylation of aryl 2‐pyridyl ethers via the loss of a 2‐pyridyloxy group is described. This method allows a 2‐pyridyloxy group to be used as a convertible directing group in C−H bond functionalization reactions. The nickel catalyst can also borylate arylmethyl 2‐pyridyl ethers, in which the stereochemistry at the benzylic position is retained in the case of chiral secondary benzylic substrates.
19.
Liang Wei Lu Yao Zuo‐Fei Wang Hua Li Hai‐Yan Tao Chun‐Jiang Wang 《Advanced Synthesis \u0026amp; Catalysis》2016,358(23):3748-3752
The first copper(I)‐catalyzed asymmetric 1,3‐dipolar [3+4] cycloaddition of nitrones with azoalkenes has been developed, affording a variety of biologically important 1,2,4,5‐oxatriazepane derivatives in good yields with exclusive regioselectivities and excellent enantioselectivities.
20.
Xiao‐Guang Song Yuan‐Yuan Ren Shou‐Fei Zhu Qi‐Lin Zhou 《Advanced Synthesis \u0026amp; Catalysis》2016,358(15):2366-2370
The first highly enantioselective intramolecular N−H bond insertion was realized by using copper catalysts modified with chiral spirobisoxazoline ligands, which provides a novel strategy for the synthesis of chiral 2‐carboxytetrahydroquinolines. This reaction features fast reaction rate, high yield, high enantioselectivity, and mild reaction conditions.