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Chemical Communications: Chem Comm

Cai-Li Sun, Hui-Qing Peng, Li-Ya Niu, Yu-Zhe Chen, Li-Zhu Wu, Chen-Ho Tung, Qing-Zheng Yang
Artificial light-harvesting nanoparticles were prepared from supramolecular polymers comprised of pillar[5]arene with anthracene-derived donors and acceptors through host-guest interactions. The resulting water-dispersible nanoparticles displayed efficient energy transfer and excellent light harvesting ability in part because the steric bulk of pillar[5]arene suppressed the self-quenching of the chromophores.
January 15, 2018: Chemical Communications: Chem Comm
M V Sulleiro, S Quiroga, D Peña, D Pérez, E Guitián, A Criado, M Prato
A non-conventional modification of exfoliated few-layer graphene (FLG) with different arynes under microwave (MW) irradiation and solvent-free conditions is reported. The described approach allows reaching fast, efficient and mild covalent functionalization of FLG.
January 15, 2018: Chemical Communications: Chem Comm
Qingzhen Yu, Pan Guo, Jie Jian, Yuye Chen, Jing Xu
Strychnofoline is a Strychnos alkaloid that has unique spirooxindole architecture and possesses important anticancer activity. Here, we have, for the first time, reported the enantioselective synthesis of strychnofoline proceeding in only nine steps from commercially available 6-methoxytryptamine. The efficiency of the synthesis derives from the use of two sequential transformation steps in the catalytic asymmetric construction of the spiro[pyrrolidine-3,3'-oxindole] motif in a facile manner. Our route is amenable to the synthesis of other natural and synthetic analogs of bioactive spirooxindole alkaloids to access their therapeutic potential...
January 15, 2018: Chemical Communications: Chem Comm
Bo-Sheng Zhang, Lu-Yao Gao, Zhe Zhang, Yu-Hua Wen, Yong-Min Liang
This report describes a new method for three-component difluoroalkylation and trifluoromethylthiolation/trifluoromethylselenolation of π-bonds via air-stable SCF3 and SeCF3 reagents as free-radical initiators of ethyl iododifluoroacetate. β-Proton elimination can be overcome effectively in this reaction system, and a broad substrate scope, including alkenes and alkynes, makes this approach practical and attractive.
January 15, 2018: Chemical Communications: Chem Comm
Giordano Rampioni, Francesca D'Angelo, Marco Messina, Alessandro Zennaro, Yutetsu Kuruma, Daniela Tofani, Livia Leoni, Pasquale Stano
Recent developments in bottom-up synthetic biology (e.g., lipid vesicle technology integrated with cell-free protein expression systems) allow the generation of semi-synthetic minimal cells (in short, synthetic cells, SCs) endowed with some distinctive capacities of natural cells. In particular, such approaches provide technological tools and conceptual frameworks for the design and engineering of programmable SCs capable of communicating with natural cells by exchanging chemical signals. Here we describe the generation of giant vesicle-based SCs which, via gene expression, synthesize in their aqueous lumen an enzyme that in turn produces a chemical signal...
January 15, 2018: Chemical Communications: Chem Comm
B Gu, A Y Khodakov, V V Ordomsky
A shift of selectivity to long chain α-olefins has been observed during Fischer-Tropsch synthesis over Co catalysts in the presence of carboxylic acids. The total selectivity to α-olefins of 39% was obtained in the presence of acids. The effect has been ascribed to intermediate formation of esters which hinder secondary olefin hydrogenation.
January 15, 2018: Chemical Communications: Chem Comm
Qian-Qian Yang, Wei Xiao, Wei Du, Qin Ouyang, Ying-Chun Chen
An efficient double catalytic system, combining chiral amine and 2-mercaptobenzoic acid, is applied for α',β-regioselective [4+2] annulations of 2-cyclopentenone with a diversity of activated alkenes, constructing multifunctional chiral bicycle[2,2,1]heptane scaffolds in good to excellent yields and enantioselectivities. In comparison with the traditional cross-dienamine species between 2-cyclopentenone and chiral amine, the interrupted enamine intermediate containing a covalently linked thiol catalyst shows significantly improved reactivity...
January 15, 2018: Chemical Communications: Chem Comm
Dian Niu, Lukang Ji, Guanghui Ouyang, Minghua Liu
A naphthalene substituted histidine derivative was found to form an organogel showing circularly polarized luminescence (CPL) and the addition of non-fluorescent achiral benzoic acids could efficiently enhance the CPL via non-covalent interactions.
January 15, 2018: Chemical Communications: Chem Comm
Xianliang Ke, Yuan Zhang, Fangliang Zheng, Yan Liu, Zhenhua Zheng, Yi Xu, Hanzhong Wang
A non-invasive labelling strategy is proposed to label baculovirus via genetic insertion of a SpyTag into the viral glycoprotein, followed by specific conjugation with the SpyCatcher protein on modified quantum dots (QDs) through an isopeptide bond. The labelling method is convenient and efficient and shows little attenuation of viral infectivity. Therefore, it is a biologically compatible technique for tracking viral infection.
January 15, 2018: Chemical Communications: Chem Comm
Mingxi Fang, Shuai Xia, Jianheng Bi, Travis P Wigstrom, Loredana Valenzano, Jianbo Wang, Wafa Mazi, Marina Tanasova, Fen-Tair Luo, Haiying Liu
An aggregation-induced emission (AIE) cyanine-based fluorescent cassette with a large pseudo-Stokes shift was designed and prepared to sensitively image pH changes in live cells via through-bond energy transfer (TBET) from a tetraphenylethene (TPE) donor to a cyanine acceptor.
January 15, 2018: Chemical Communications: Chem Comm
Zoe R Todd, Albert C Fahrenbach, Christopher J Magnani, Sukrit Ranjan, Anders Björkbom, Jack W Szostak, Dimitar D Sasselov
UV-driven photoredox processing of cyanocuprates can generate simple sugars necessary for prebiotic synthesis. We investigate the wavelength dependence of this process from 215 to 295 nm and generally observe faster rates at shorter wavelengths. The most efficient wavelengths are accessible to a range of potential prebiotic atmospheres, supporting the potential role of cyanocuprate photochemistry in prebiotic synthesis on the early Earth.
January 15, 2018: Chemical Communications: Chem Comm
Sharareh Bagherzadeh, Neal P Mankad
Oxidation of a [Cu2(μ-S)] complex by N2O or CO2 generated a [Cu2(μ-SO4)] product. In the presence of a sulfur trap, a [Cu2(μ-O)] species also formed from N2O. A [Cu2(μ-CS3)] species derived from CS2 modeled initial reaction intermediates. These observations indicate that one role of tetranuclearity in the CuZ catalytic site of nitrous oxide reductase is to protect the crucial S2- ligand from oxidation.
January 15, 2018: Chemical Communications: Chem Comm
Lewis MacDonald, Benjamin Rausch, Mark D Symes, Leroy Cronin
The 2-electron reduced form of the polyoxometalate silicotungstic acid (H4[SiW12O4]) is shown to be an effective and selective hydrogenation agent for a range of nitroarenes without the need for any co-catalyst. The ease of generation of the active species and its recyclability suggest that a new approach to this important class of chemical conversions is possible.
January 15, 2018: Chemical Communications: Chem Comm
Ti-Long Yang, Shao-Fei Ni, Peng Qin, Li Dang
Density functional theory (DFT) calculations show that H2 evolution is attributed to active sulfur hydrides derived from MoS2 complexes via two- or three-electron reduction from the synthesized [(PY5Me2)MoS2]2+. Water acts as a bridge for H2 evolution from the intermolecular H+/H- coupling between sulfur hydride complexes and hydrated protons.
January 15, 2018: Chemical Communications: Chem Comm
Rui Wang, Fang Zhang, Cheng Qian, Cui Wu, Zunzhong Ye, Liu Wang, Wenjuan Qian, Jianfeng Ping, Jian Wu, Yibin Ying
An ultrafast and extremely simple approach was proposed to count the number of DNA molecules without any microfluidic-based device. By directly counting the number of amplicon clusters in a capillary, the absolute amount of DNA molecules could be easily determined.
January 15, 2018: Chemical Communications: Chem Comm
Aaron D Proctor, Shobhana Panuganti, Bart M Bartlett
The aerobic photochemical oxidation of benzylamine was carried out on the ternary oxides CuWO4 and BiVO4 as a test proton-coupled-electron-transfer reaction in acetonitrile. Both oxides give the coupled imine product, N-benzylidenebenzylamine, in near quantitative (98-99%) yield, with rate constants of 0.34 h-1 g-1 and 0.70 h-1 g-1 for CuWO4 and BiVO4, respectively.
January 15, 2018: Chemical Communications: Chem Comm
Hiroyuki Suga, Taichi Iwai, Masahiro Shimizu, Kie Takahashi, Yasunori Toda
An efficient method for the generation of an oxidopyrylium ylide from 6-acetoxy-6-acetoxymethyl-2H-pyran-3(6H)-one using a Pd catalyst and [5+2] cycloadditions of the resulting ylide are described. Among substituted styrene derivatives as dipolarophiles, electron-rich styrenes showed higher yield (up to 80%). The [5+2] cycloaddition reactions can also be applied to exo-methylene cyclic compounds, and an improved method for the synthesis of polygalolide intermediate has been demonstrated.
January 15, 2018: Chemical Communications: Chem Comm
Neal P Mankad
The rational development of catalytic reactions involving cooperative behavior between two catalytic reactive sites represents a frontier area of research from which novel reactivity and selectivity patterns emerge. Within this context, this Feature highlights the development of a cooperative system involving transition metal Lewis acid/base pairs. Bimetallic systems consisting of copper carbene Lewis acids and metal carbonyl anion Lewis bases, (NHC)Cu-[MCO], are easily synthesized from readily available organometallic building blocks (NHC = N-heterocyclic carbene; [MCO]- = metal carbonyl anion, e...
January 15, 2018: Chemical Communications: Chem Comm
Abhishek Koner, Zsolt Kelemen, Gregor Schnakenburg, László Nyulászi, Rainer Streubel
The dienic nature of the aromatic π-system in 1,4-diphosphinines remains largely unexplored to this day due to a lack of facile and efficient synthetic protocols. Recently reported stable, tricyclic 1,4-diphosphinines were used to explore the thermal reactivity of the π-system towards an array of dienophiles in [4π+2π]- and, for the first time, in [4π+2σ]-type cycloaddition reactions.
January 12, 2018: Chemical Communications: Chem Comm
Yuan Yang, Ren-Jie Song, Yang Li, Xuan-Hui Ouyang, Jin-Heng Li, De-Liang He
A copper-catalyzed oxidative radical strategy to avoid the use of the highly expensive noble metal/ligand catalytic systems is described, which allows selective activation of dual chemical bonds around the Si-atom center relying on the nature of alkylsilanes. While for tertiary silanes selective functionalization of Si-H/silyl C(sp3)-H bonds in intermolecular oxidative annulation cascades with N-(2-(ethynyl)aryl)acrylamides toward silino[3,4-c]quinolin-5(3H)-ones, when using secondary silanes and HSi(TMS)3, dual Si-H bonds or Si-H/Si-Si bonds are selectively cleaved leading to 4H-silolo[3,4-c]quinolin-4-ones...
January 12, 2018: Chemical Communications: Chem Comm
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