Organic Letters
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6.09
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#1Yanmeng Zhang (CCNU: Central China Normal University)
#2He Zhang (CCNU: Central China Normal University)
Last. Ke Gao (CCNU: Central China Normal University)
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We report herein that a borane-trimethylamine complex worked as an efficient reducing agent for the selective methylation and formylation of amines with 1 atm CO2 under metal-free conditions. 6-Amino-2-picoline serves as a highly efficient catalyst for the methylation of various secondary amines, whereas in its absence, the formylation of primary and secondary amines was achieved in high yield with high chemoselectivity. Mechanistic studies suggest that the 6-amino-2-picoline-borane catalytic sy...
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#1Hai-Jiao Long (Chongqing University)
#2Yin-Long Li (Chongqing University)
Last. Jun Deng (Chongqing University)
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The catalytic enantioselective desymmetrizing bromoaminocyclization of prochiral cyclohexa-1,4-dienes has been achieved by using chiral anion phase-transfer catalysis, providing a range of enantioenriched cis-3a-arylhydroindoles bearing an all-carbon quaternary stereocenter in good yields (up to 78%) and excellent enantioselectivities (up to 97% ee). Furthermore, the potential application of this methodology to natural product total synthesis was demonstrated by the asymmetric synthesis of (+)-M...
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#1Miao LiH-Index: 1
#2Dong YaqunH-Index: 2
Last. Song SunH-Index: 17
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An iridium-catalyzed redox-neutral C-2 and C-3 dual C-H functionalization of indoles with nitrones has been developed, furnishing a range of 7H-indolo[2,3-c]quinolines with high efficiency and regioselectivity under mild reaction conditions. Notably, sequential multiple C-H bond cleavage and C-C bond formation constitute the key events of this process, in which nitrone serves as a building block and an oxidant. Distinct from the previous methods toward 7H-indolo[2,3-c]quinolines, this newly deve...
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#1Wing Ho So (CUHK: The Chinese University of Hong Kong)H-Index: 3
#2Yishu Bao (CUHK: The Chinese University of Hong Kong)
Last. Jiang Xia (CUHK: The Chinese University of Hong Kong)H-Index: 26
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Here we report a method to synthesize C-terminally modified peptides on resin. A four-component Ugi reaction of isocyanide resin, an Fmoc-protected amino acid, an amine, and a 6-nitroveratrylaldehyde gives C-terminal photocaged peptide amides, which can be photolyzed to generate C-terminal peptide amides. Changing the amine component in the Ugi reaction gives peptides with different C-terminal modifications including substituted anilides, alkyne, and azide. By installing an N-terminal azide and ...
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#1Xiaoqin Ning (Sichuan University)
#2Yongke Chen (Sichuan University)
Last. Ying Xia (Sichuan University)H-Index: 29
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Described herein are the palladium-catalyzed cross-coupling reactions of cyclobutanone-derived N-sulfonylhydrazones with aryl or benzyl halides, suggesting that the metal carbene process and β-hydride elimination can smoothly occur in strained ring systems. Structurally diversified products including cyclobutenes, methylenecyclobutanes, and conjugated dienes are selectively afforded in good to excellent yields. Preliminary success in asymmetric carbene coupling reactions in strained ring systems...
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#1Jinhui Ma (JNU: Jinan University)H-Index: 1
#2Jiajun Luo (SCUT: South China University of Technology)
Last. Biaolin Yin (SCUT: South China University of Technology)H-Index: 18
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The syntheses of polycyclic thienoindolines bearing a dihydrothiophene or tetrahydrothiophene subunit have not been reported, despite the fact that such compounds may have interesting medicinal properties. Herein, we report a protocol for accessing polycyclic dihydrothiophenes by means of formal [2+2+1] intramolecular dearomatizing cyclization of alkynyl indoles with K2S and S8 as the sources of sulfide. In addition, tetrahydrothienoindolines were stereoselectively synthesized via a one-pot, two...
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#1Hetao Xu (FZU: Fuzhou University)
#2Mingxing Ye (FZU: Fuzhou University)
Last. Qiuling Song (FZU: Fuzhou University)H-Index: 31
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Herein we present a transition-metal-free cross-coupling reaction of isatogens with boronic acids through a 1,4-metalate shift of a boron "ate" complex. This coupling reaction provides a feasible method to deliver valuable 2,2-disubstituted indolin-3-one derivatives with excellent regioselectivity, which exhibit operational simplicity, good functional group tolerance, and a broad substrate scope.
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#1Zhenjie Qi (NU: Nanjing University)
#2Shaozhong Wang (NU: Nanjing University)H-Index: 18
Chemodivergent reactions of oximes and diazo esters involving Rh-catalyzed [3+2] annulation and photodriven O-H insertion have been developed to generate oxazoles and oxime ethers. A range of aldehyde and ketone oximes reacted with α-diazocarbonyl compounds in a controllable manner in which functional groups, including ketone, ester, amide, ether, thiol ether, silane, alkene, allene, and alkyne groups, were well tolerated.
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#1Heyun Sheng (Huaqiao University)
#2Jianke Su (Huaqiao University)H-Index: 1
Last. Qiuling Song (CAS: Chinese Academy of Sciences)H-Index: 31
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We report herein an efficient strategy to construct 3-(2,2-difluoroethyl)-2-fluoroindoles from activated o-aminostyrenes with ethyl bromodi-fluoroacetate as a difluorocarbene source. Through double capture of a difluorocarbene, two different types of fluorine motifs are incorporated into the products with simultaneous construction of one C-N and two C-C bonds, without the need for transition metals. This reaction features high efficiency and excellent functional group compatibility and has great...
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#1Kai Ji (SJTU: Shanghai Jiao Tong University)
#2Ka Lu (Lanzhou University)
Last. Zhi-Min Chen (Lanzhou University)H-Index: 17
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A Bronsted acid-catalyzed 1,4-addition hydrothiolation of branched 1,3-dienes was explored for the first time. A solvent-controlled divergent synthesis of sulfides is also disclosed. Use of acetonitrile as a solvent gave allylic sulfides as hydrothiolation products, while thiochromane derivatives (hydrothiolation/Friedel-Crafts products) were obtained using dichloromethane as the solvent. The origin of the regioselectivity of hydrothiolation was explored through density functional theory calcula...
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