- Sequential Addition of Amines to Nitrile and Carbon-Carbon Multiple Bond: A Route to 7-Amino-5 H-dibenzo[ c,e]azepines
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A rare earth metal-catalyzed sequential inter- and intramolecular C-N bond formation of 2-nitrile-2′-alkenyl(alkynyl)biphenyls with amines has been developed, which provides a straightforward and efficient access to a range of new functional dibenzo[c,e]azepines. This represents the first examples of direct construction of seven-membered azaheterocycle from unsaturated nitriles and amines. Such transformations have the advantages of avoiding the use of additives, easily available starting materials, step- and high atom-economy, mild reaction conditions, and high selectivity.
- Hu, Kun,Liu, Ruiting,Zhou, Xigeng
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supporting information
p. 6946 - 6950
(2021/09/11)
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- Controlling the Selectivity Patterns of Au-Catalyzed Cyclization-Migration Reactions
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As little as 2 mol % of (XPhos)AuNTf2 catalyzes the transformation of a broad range of o-acetylene-substituted styrenes into 1,2-dihydronaphthalenes. Our data suggests that this transformation occurs via a gold-stabilized cyclopropyl carbinyl cation, which triggers either a [1,2] carboxylate shift or a less favorable [1,2] aryl shift. The relative rates of these migrations can be controlled by the identity of the ligand or by stabilizing the mesomeric cation.
- Chen, Mo,Su, Naijing,Deng, Tianning,Wink, Donald J.,Zhao, Yingwei,Driver, Tom G.
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supporting information
p. 1555 - 1558
(2019/03/20)
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- Enantioselective Folding of Enynes by Gold(I) Catalysts with a Remote C2-Chiral Element
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Chiral gold(I) catalysts have been designed based on a modified JohnPhos ligand with a distal C2-2,5-diarylpyrrolidine that creates a tight binding cavity. The C2-chiral element is close to where the C-C bond formation takes place in cyclizations of 1,6-enynes. These chiral mononuclear catalysts have been applied for the enantioselective 5-exo-dig and 6-endo-dig cyclization of different 1,6-enynes as well as in the first enantioselective total synthesis of three members of the carexane family of natural products. Opposite enantioselectivities have been achieved in seemingly analogous reactions of 1,6-enynes, which result from different chiral folding of the substrates based on attractive aryl-aryl interactions.
- Zuccarello, Giuseppe,Mayans, Joan G.,Escofet, Imma,Scharnagel, Dagmar,Kirillova, Mariia S.,Pérez-Jimeno, Alba H.,Calleja, Pilar,Boothe, Jordan R.,Echavarren, Antonio M.
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supporting information
p. 11858 - 11863
(2019/08/20)
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- Gold(I)-Catalyzed Cascade Cyclization Reactions of Allenynes for the Synthesis of Fused Cyclopropanes and Acenaphthenes
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A gold-catalyzed reaction of phenylene-tethered allenynes with benzofurans gave 1-(naphth-1-yl)cyclopropa[b]benzofuran derivatives, whereas the reaction of 1-allenyl-2-ethynyl-3-methylbenzene derivatives in the absence of benzofurans gave acenaphthenes in good yields. These results can be rationalized by nucleophilic attack of the alkyne moiety on an activated allene to form a vinyl cation intermediate.
- Ikeuchi, Takaya,Inuki, Shinsuke,Oishi, Shinya,Ohno, Hiroaki
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supporting information
p. 7792 - 7796
(2019/05/15)
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- Gold-catalyzed cycloisomerization of pyridine-bridged 1,8-diynes: An expedient access to luminescent cycl[3.2.2]azines
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Gold-catalyzed diyne cycloisomerizations involving carbene/alkyne metathesis have been the focal point of attention for the past few years as it offers great potential to build complex polycyclic architectures. However, the design of novel cycloisomerizations has been mostly limited to 1,5/1,6-diynes and has remained very challenging to apply for higher 1,n-diynes. Herein, we disclose an unprecedented cycloisomerization of pyridine-bridged 1,8-diynes involving carbene/alkyne metathesis to access luminescent cycl[3.2.2]azines.
- Chintawar, Chetan C.,Mane, Manoj V.,Tathe, Akash G.,Biswas, Suprakash,Patil, Nitin T.
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supporting information
p. 7109 - 7113
(2019/09/30)
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- A new class of N-doped ionic PAHs: Via intramolecular [4+2]-cycloaddition between arylpyridines and alkynes
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Reported herein, for the first time, is a copper-promoted intramolecular [4+2]-cycloaddition cascade to access ionic N-doped polycyclic aromatic hydrocarbons (PAHs) with tunable emission wavelengths. It is shown that the reaction can be made catalytic with respect to Cu(OTf)2 when an external oxidant, Selectfluor, was used.
- Mule, Ravindra D.,Shaikh, Aslam C.,Gade, Amol B.,Patil, Nitin T.
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supporting information
p. 11909 - 11912
(2018/11/10)
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- Oxidative Intramolecular 1,2-Amino-Oxygenation of Alkynes under AuI/AuIIICatalysis: Discovery of a Pyridinium-Oxazole Dyad as an Ionic Fluorophore
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Oxidative intramolecular 1,2-amino-oxygenation reactions, combining gold(I)/gold(III) catalysis, is reported. The reaction provides efficient access to a structurally unique ionic pyridinium-oxazole dyad with tunable emission wavelengths. The application of these fluorophores as potential biomarkers has been investigated.
- Shaikh, Aslam C.,Ranade, Dnyanesh S.,Rajamohanan, Pattuparambil R.,Kulkarni, Prasad P.,Patil, Nitin T.
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supporting information
p. 757 - 761
(2017/01/14)
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- ORGANIC COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME
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The present invention relates to a novel compound represented by chemical formula 1 and an organic electroluminescent device comprising the same. According to the present invention, the compound is used in an organic material layer of the organic electroluminescent device, desirably a hole transport layer and an electron retarding layer, thereby improving light emitting efficiency, driving voltage, lifespan, etc of the organic electroluminescent device.COPYRIGHT KIPO 2015
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Paragraph 0147-0149
(2016/10/10)
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