- Tertiary amines acting as Alkyl radical equivalents enabled by a P/N heteroleptic Cu(I) photosensitizer
-
An unprecedented exploration of tertiary amines as alkyl radical equivalents for cross-coupling with aromatic alkynes to access allylarenes has been achieved by a P/N heteroleptic Cu(I)based photosensitizer under photoredox catalysis conditions. Mechanist
- Zheng, Limeng,Jiang, Qinfang,Bao, Hanyang,Zhou, Bingwei,Luo, Shu-Ping,Jin, Hongwei,Wu, Huayue,Liu, Yunkui
-
p. 8888 - 8893
(2020/11/30)
-
- Sulfuryl Fluoride Mediated Conversion of Aldehydes to Nitriles
-
Aliphatic, aromatic, and heteroaromatic aldehydes were readily converted to corresponding nitriles in a one-pot reaction sequence with hydroxylamine and sulfuryl fluoride. The reaction proceeds at room temperature, does not require metal catalysts and special precautions, and produces nitriles in excellent yields. It is compatible with a variety of functional groups, can be performed in aqueous and organic solvents, and is readily scalable to multigram quantities. Mild conditions and high selectivity of the reaction enabled the construction of polyfunctional probes containing nitrile, alkyne, azide, and fluorosulfate groups for further orthogonal derivatization.
- Gurjar, Jitendra,Bater, Jorick,Fokin, Valery V.
-
supporting information
p. 1906 - 1909
(2019/01/24)
-
- Lanthanide-Catalyzed Tandem Insertion of Secondary Amines with 2-Alkynylbenzonitriles: Synthesis of Aminoisoindoles
-
A lanthanide-catalyzed intermolecular hydroamination of 2-alkynylbenzonitriles with secondary amines has been disclosed, providing a streamlined access to a range of aminoisoindoles in moderate to excellent yields. The salient features of this reaction in
- Ye, Pengqing,Shao, Yinlin,Xie, Leping,Shen, Keting,Cheng, Tianxing,Chen, Jiuxi
-
p. 3681 - 3690
(2018/11/23)
-
- Gold(i)-catalyzed cross-coupling reactions of aryldiazonium salts with organostannanes
-
Gold(i)-catalyzed cross-coupling reactions of aryldiazonium salts with organostannanes are described. This redox neutral strategy offers an efficient approach to diverse biaryls, vinyl arenes and arylacetylenes. Monitoring the reaction with NMR and ESI-MS provided strong evidence for the in situ formation of Ph3PAuIR (R = aryl, vinyl and alkynyl) species which is crucial for the activation of aryldiazonium salts.
- Akram, Manjur O.,Shinde, Popat S.,Chintawar, Chetan C.,Patil, Nitin T.
-
supporting information
p. 2865 - 2869
(2018/05/03)
-
- Synthesis of N-Heteroaromatic Compounds through Cyclocarbonylative Sonogashira Reactions
-
A protocol based on cyclocarbonylative Sonogashira reactions has been developed for the synthesis of nitrogen-containing heterocycles. The process is carried out under CO pressure, in the presence of a small amount of PdCl2(PPh3)sub
- Aronica, Laura Antonella,Albano, Gianluigi,Giannotti, Luca,Meucci, Elisa
-
p. 955 - 963
(2017/02/15)
-
- Synthesis of naphthalene amino esters and arylnaphthalene lactone lignans through tandem reactions of 2-alkynylbenzonitriles
-
Tandem reaction of 2-alkynylbenzonitriles with a Reformatsky reagent turned out to be a novel and efficient approach toward 1-aminonaphthalene-2- carboxylates. Interestingly, with 2-(3-hydroxyprop-1-ynyl)benzonitriles as the substrates, a more sophisticat
- He, Yan,Zhang, Xinying,Fan, Xuesen
-
supporting information
p. 5641 - 5643
(2014/05/20)
-
- Layer-type organosilver(I) complexes assembled with nitrate and functionalized phenylethynide ligands
-
A series of seven silver(I) nitrate complexes containing new ligands each composed of a functionalized phenyl nucleus bearing a terminal ethynyl substituent has been synthesized and characterized by single-crystal X-ray analysis. The coordination preferen
- Cheng, Ping-Shing,Hau, Sam C.K.,Mak, Thomas C.W.
-
p. 110 - 119
(2013/07/27)
-
- Metal-free oxidative trifluoromethylthiolation of terminal alkynes with CF3SiMe3 and elemental sulfur
-
A metal-free oxidative trifluoromethyl-thiolation of terminal alkynes using readily available CF3SiMe3 and elemental sulfur at room temperature has been developed. This reaction provides an efficient and convenient method for the preparation of alkynyl trifluoromethyl sulfides bearing a wide range of functional groups. Preliminary investigation revealed that elemental sulfur instead of air acted as the oxidant.
- Chen, Chao,Chu, Lingling,Qing, Feng-Ling
-
p. 12454 - 12457
(2012/09/05)
-
- Formation of indoles, dihydroisoquinolines, and dihydroquinolines by ruthenium-catalyzed heterocyclizations
-
Indoles, dihydroisoquinolines, and dihydroquinolines were efficiently prepared by ruthenium-catalyzed heterocyclizations of aromatic homo- and bis-homopropargyl amines/amides in the presence of an amine/ammonium base-acid pair. These regioselective 5-endo and 6-endo cyclizations most probably occur by nucleophilic trapping of key ruthenium-vinylidene intermediates. Georg Thieme Verlag Stuttgart · New York.
- Varela-Fernández, Alejandro,Varela, Jesús A.,Saá, Carlos
-
p. 3285 - 3295
(2013/01/15)
-
- Ruthenium-catalyzed cycloisomerization of aromatic homo- and bis-homopropargylic amines/amides: Formation of indoles, dihydroisoquinolines and dihydroquinolines
-
Ruthenium-catalyzed cycloisomerizations of aromatic homo- and bis-homopropargylic amines/amides efficiently afford indoles, dihydroisoquinolines and dihydroquinolines. These processes were regioselective (5- and 6-endo cyclizations) on using key Ru vinylidene intermediates. The presence of an amine/ammonium base-acid pair increased the rate of cyclization and facilitated the catalytic turnover. Copyright
- Varela-Fernandez, Alejandro,Varela, Jesus A.,Saa, Carlos
-
p. 1933 - 1937
(2011/10/08)
-
- Copper-catalyzed cross-coupling of alkyl and aryl grignard reagents with alkynyl halides
-
(Chemical Equation Presented) Good old copperl A new general procedure to couple aliphatic and aromatic Grignard reagents with alkynyl halides under copper catalysis is described (see scheme; NMP=N-methylpyrrolidinone). The reaction is chemoselective and allows preparation of a vast array of simple and functionalized internal alkynes in high yields.
- Cahiez, Gerard,Gager, Olivier,Buendia, Julien
-
supporting information; experimental part
p. 1278 - 1281
(2010/05/18)
-
- A chemical dynamics, kinetics, and theoretical study on the reaction of the cyano radical (CN; X2Σ+) with phenylacetylene (C6H5CCH; X1A1)
-
The chemical reaction dynamics to form o-, m-, and p-cyanophenylacetylene via the neutral-neutral reaction of ground state cyano radicals with phenylacetylene and D1-phenylacetylene were investigated in crossed beam experiments; these studies were combined with kinetics measurements of the rate coefficients at temperatures of 123, 200, and 298 K and supplemented by electronic structure calculations. The data suggest that the reaction is initiated by a barrier-less addition of the electrophilic cyano radical to the o-, m-, or p-position of the aromatic ring. The eventually fragmented via atomic hydrogen elimination to form o-, m-, and p-cyanophenylacetylene via tight exit transition states with the hydrogen atom being ejected almost perpendicularly to the molecular plane of the rotating complex. The overall reaction to form o-, m-, and p-cyanophenylacetylene was found to be exoergic by 89 ± 18 kJ mol-1 in nice agreement with the calculations. The o-cyanophenylacetylene isomer is of particular relevance as a potential building block to the formation of nitrogen-substituted didehydronaphthalene molecules in analogy to didehydronaphthalene in Titan's aerosol layers - a pathway hitherto neglected by the planetary science modeling community.
- Bennett, Chris J.,Morales, Sebastien B.,Le Picard, Sebastien D.,Canosa, Andre,Sims, Ian R.,Shih,Chang,Gu, Xibin,Zhang, Fantong,Kaiser, Ralf I.
-
experimental part
p. 8737 - 8749
(2011/04/26)
-
- Block modification of rod-shaped π conjugated carbon frameworks with donor and acceptor groups toward highly fluorescent molecules: Synthesis and emission characteristics
-
To create organic molecules that are highly fluorescent at a longer wavelength region, we investigated the synthesis (using Pd-catalyzed cross-coupling) and photophysical properties (Φ f, λ em, τ , λ abs, and ε ) of the following π conjugated molecular rods consisting of p-phenyleneethynylene units modified by donor (OMe) and/or acceptor (CN) groups: (1) side-donor modification systems (SD systems), (2) side-acceptor modification systems (SA systems), and (3) systems consisting of a donor block and an acceptor block (BL systems). As a consequence, very high Φ f values (>0.95) were obtained for BL systems. Bathochromic shifts of λ em for the same π conjugation length were largest for BL systems. Thus we succeeded in creating highly efficient light emitters at a longer wavelength region by block modification (e.g., Φ f = 0.97, λ em = 464 nm for BL-9). Considerably intense solid emission (Φ f ～ 0.5) at a longer wavelength region (500- 560 nm) was also found for BL systems. It has been found that BL-6 and BL-8 exhibit interesting two photon absorption characteristics. This journal is The Royal Society of Chemistry.
- Ochi, Takanori,Yamaguchi, Yoshihiro,Wakamiya, Tateaki,Matsubara, Yoshio,Yoshida, Zen-Ichi
-
supporting information; scheme or table
p. 1222 - 1231
(2008/10/09)
-
- New fluorophores with rod-shaped polycyano π-conjugated structures: Synthesis and photophysical properties
-
Novel rod-shaped polycyano-oligo(phenyleneethynylene)s were synthesized by Pd cross-coupling reaction. Polycyano groups were found to greatly improve the emission efficiency (Φf) of OPEs. By the end donor modification, we achieved the creation of very intense blue light-emitting fluorophore with the SMe group (Φf) = 0.972, log ε 4.89, λ em 455 nm) and very intense yellow light-emitting fluorophore with the NMe2 group (Φf = 0.999, log ε 4.75, λem 555 nm). Contrasting Φf solvent dependency of 6 and 7 and a linear relationship between Φf and σp-X over the whole region of σp-X were also found.
- Yamaguchi, Yoshihiro,Ochi, Takanori,Wakamiya, Tateaki,Matsubara, Yoshio,Yoshida, Zen-Ichi
-
p. 717 - 720
(2007/10/03)
-
- HETEROCYCLIC COMPOUNDS HAVING AN OXADIAZOLE MOIETY AND HYDRO ISOMERS THEREOF
-
The present invention relates to substituted diphenyl heterocycle compounds having an oxadiazole moiety and pharmaceuticals compositions thereof that inhibit replication of HCV virus. The present invention also relates to the use of the compounds and/or compositions to inhibit HCV replication and/or proliferation and to treat or prevent HCV infections.
- -
-
-
- Pharmaceutical compositions comprising aryl-substituted acyclic enediyne compounds
-
A pharmaceutical compositions comprises a compound of formula (I): or a pharmaceutically acceptable salt thereof: wherein R1═R2 ═H; or R1 and R2 together form a moiety represented by the formula R3 re
- -
-
Page/Page column 15
(2008/06/13)
-
- Microwave-assisted in situ deprotection and ω-methoxylation of TMS-protected aryl alkynes
-
Using microwave technology, rapid ω-methoxylation of aryl alkynes is possible.
- Wettergren, Jenny,Minidis, Alexander B. E.
-
p. 7611 - 7612
(2007/10/03)
-
- Synthesis and preliminary testing of molecular wires and devices
-
Presented here are several convergent synthetic routes to conjugated oligo(phenylene ethynylene)s. Some of these oligomers are free of functional groups, while others possess donor groups, acceptor groups, porphyrin interiors, and other heterocyclic interiors for various potential transmission and digital device applications. The syntheses of oligo(phenylene ethynylene)s with a variety of end groups for attachment to numerous metal probes and surfaces are presented. Some of the functionalized molecular systems showed linear, wire-like, current versus voltage (I(V)) responses, while others exhibited nonlinear I(V) curves for negative differential resistance (NDR) and molecular random access memory effects. Finally, the syntheses of functionalized oligomers are described that can form self-assembled monolayers on metallic electrodes that reduce the Schottky barriers. Information from the Schottky barrier studies can provide useful insight into molecular alligator clip optimizations for molecuar electronics.
- Tour, James M.,Rawlett, Adam M.,Kozaki, Masatoshi,Yao, Yuxing,Jagessar, Raymond C.,Dirk, Shawn M.,Price, David W.,Reed, Mark A.,Zhou, Chong-Wu,Chen, Jia,Wang, Wenyong,Campbell, Ian
-
p. 5118 - 5134
(2007/10/03)
-
- Double anionic cycloaromatization of 2-(6-substituted-3-hexene-1,5-diynyl)-benzonitriles initiated by methoxide addition
-
Formula presented Treatment of 2-((3Z)-undecene-1,5-diynyl)benzonitrile with 5 equiv of sodium methoxide in refluxing methanol for 16 h gave 1-pentyl-6-methoxyphenanthridine in 12% yield, 1-pentyl-6-phenanthridone in 6% yield, and 2-(2-pentyl-6-methoxyphe
- Wu, Ming-Jung,Lin, Chi-Fong,Chen, Shang-Hung
-
p. 767 - 768
(2008/02/12)
-
- Association of dicyanodiphenylacetylenes with silver(I) salts in solution and solid state: Electrospray ionization mass spectrometry samples aggregates at subsaturated concentrations
-
Complexes of 2,3'-dicyanodiphenylacetylene (2,3'-DCPA, 1), 2,2'-dicyanodiphenylacetylene (2,2'-DCPA, 2), and 2,4'-dicyanodiphenylacetylene (2,4'-DCPA, 3) with silver(I) salts have been characterized in the solid state by single-crystal X-ray analysis. In
- Hirsch, Keith A.,Wilson, Scott R.,Moore, Jeffrey S.
-
p. 10401 - 10412
(2007/10/03)
-
