- Transition Metal-Free Regioselective Remote C?H Bond 2,2,2-Trifluoroethoxylation of 8-Aminoquinoline Derivatives at the C5 Position
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The regioselective 2,2,2-trifluoroethoxylation at the C5 position of amides derived from the 8-aminoquinoline has been developed. In the presence of PIDA, an unprecedented and undirected transition metal-free transformation was achieved using the readily available and appealing 2,2,2-trifluoroethanol as the fluorinated source. The selective distal 2,2,2-trifluoroethoxylation of an array of amides was achieved in moderate to good yields (12 examples, up to 61 % yield). This approach provided efficient access to high-value added fluorinated quinoline derivatives, key building blocks for bulk and fine chemical industry.
- Ruyet, Louise,Poisson, Thomas,Besset, Tatiana
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supporting information
p. 3407 - 3410
(2021/06/28)
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- Palladium-Catalyzed H/D Exchange Reaction with 8-Aminoquinoline as the Directing Group: Access to ortho-Selective Deuterated Aromatic Acids and β-Selective Deuterated Aliphatic Acids
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We develop a palladium-catalyzed H/D exchange reaction with 8-aminoquinoline as the directing group as well as D2O as the source of deuterium atom and solvent. This reaction achieves selectively H/D exchange at the ortho-C-H of aromatic amides and the β-C-H of aliphatic amide. Ortho-deuterated aromatic acids and β-deuterated aliphatic acids are obtained by removal of the directing group. And a possible mechanism is also proposed.
- Zhao, Donghong,Luo, Haofan,Chen, Binhui,Chen, Wenteng,Zhang, Guolin,Yu, Yongping
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p. 7860 - 7866
(2018/07/21)
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- Stereoselective synthesis of diazabicyclic β-lactams through intramolecular amination of unactivated C(sp3)-H bonds of carboxamides by palladium catalysis
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An efficient C(sp3)-H bond activation and intramolecular amination reaction via palladium catalysis at the β-position of carboxyamides to make β-lactams was described. The investigation of the substrate scope showed that the current reaction conditions favored activation of the β-methylene group. Short sequences were developed for preparation of various diazabicyclic β-lactam compounds with this method as the key step from chiral proline and piperidine derivatives.
- Zhang, Shi-Jin,Sun, Wen-Wu,Cao, Pei,Dong, Xiao-Ping,Liu, Ji-Kai,Wu, Bin
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p. 956 - 968
(2016/02/19)
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- Cobalt-Catalyzed sp2-C?H Activation: Intermolecular Heterocyclization with Allenes at Room Temperature
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The reactivity of allenes in transition-metal-catalyzed C?H activation chemistry is governed by the formation of either alkenyl–metal (M–alkenyl) or metal–π-allyl intermediates. Although either protonation or a β-hydride elimination is feasible with a M–alkenyl intermediate, cyclization has remained unexplored to date. Furthermore, due to the increased steric hindrance, the regioselectivity for the intramolecular cyclization of the metal–π-allyl intermediate was hampered towards the more substituted side. To address these issues, a unified approach to synthesize a diverse array of biologically and pharmaceutically relevant heterocyclic moieties by cobalt-catalyzed directed C?H functionalization was envisioned. Upon successful implementation, the present strategy led to the regioselective formation of dihydroisoquinolin-1(2H)-ones, isoquinolin-1(2H)-ones, dihydropyridones, and pyridones.
- Thrimurtulu, Neetipalli,Dey, Arnab,Maiti, Debabrata,Volla, Chandra M. R.
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supporting information
p. 12361 - 12365
(2016/10/13)
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- Cobalt-catalyzed, aminoquinoline-directed C(sp2)-H bond alkenylation by alkynes
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A method for cobalt-catalyzed, aminoquinoline- and picolinamide-directed C(sp2)-H bond alkenylation by alkynes was developed. The method shows excellent functional-group tolerance and both internal and terminal alkynes are competent substrates for the coupling. The reaction employs a Co(OAc)2·4 H2O catalyst, Mn(OAc)2 co-catalyst, and oxygen (from air) as a terminal oxidant.
- Grigorjeva, Liene,Daugulis, Olafs
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p. 10209 - 10212
(2015/03/31)
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- Cobalt-catalyzed direct carbonylation of aminoquinoline benzamides
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A method for direct carbonylation of aminoquinoline benzamides has been developed. Reactions proceed at room temperature in trifluoroethanol solvent, use oxygen from air as an oxidant, and require Mn(OAc)3 as a cocatalyst. Benzoic and acrylic a
- Grigorjeva, Liene,Daugulis, Olafs
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supporting information
p. 4688 - 4690
(2015/01/08)
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- Palladium-catalyzed direct ortho -alkynylation of aromatic carboxylic acid derivatives
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The palladium-catalyzed direct alkynylation of C-H bonds in aromatic carboxylic acid derivatives is described. The use of 8-aminoquinoline as a directing group facilitates the alkynylation of an electronically diverse range of C(sp2)-H bonds.
- Ano, Yusuke,Tobisu, Mamoru,Chatani, Naoto
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p. 354 - 357
(2012/03/09)
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