- One-Pot Synthesis and Conformational Analysis of Six-Membered Cyclic Iodonium Salts
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Two one-pot procedures for the construction of carbon-bridged diaryliodonium triflates and tetrafluoroborates are described. Strong Br?nsted acids enable the effective Friedel-Crafts alkylation with diversely substituted o-iodobenzyl alcohol derivatives, providing diphenylmethane scaffolds, which are subsequently oxidized and cyclized to the corresponding dibenzo[b,e]iodininium salts. Based on NMR investigations and density functional theory (DFT) calculations, we could verify the so-far-undescribed existence of two stable isomers in cyclic iodonium salts substituted with aliphatic side chains in the carbon bridge.
- Caspers, Lucien D.,Spils, Julian,Damrath, Mattis,Lork, Enno,Nachtsheim, Boris J.
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p. 9161 - 9178
(2020/08/14)
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- Palladium-catalyzed arylation of 1,4-naphthoquinones with aryl iodides and its synthetic application to the benzo[b]phenanthridine skeleton
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We report a Pd-catalyzed arylation of 1,4-naphthoquinones with aryl iodides. This reaction shows excellent functional group tolerance and high regioselectivity when using nonsymmetric 1,4-naphthoquinone. Furthermore, the resulting 2-aryl-1,4-naphthoquinon
- Akagi, Yusuke,Komatsu, Toshiya
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supporting information
(2020/10/02)
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- KMnO4-catalyzed chemoselective deprotection of acetate and controllable deacetylation-oxidation in one pot
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A novel and efficient protocol for chemoselective deacetylation under ambient conditions was developed using catalytic KMnO4. The stoichiometric use of KMnO4 highlighted the dual role of a heterogeneous oxidant enabling direct access to aromatic aldehydes in one-pot sequential deacetylation-oxidation. The reaction employed an alternative solvent system and allowed the clean transformation of benzyl acetate to sensitive aldehyde in a single step while preventing over-oxidation to acids. Use of inexpensive and readily accessible KMnO4 as an environmentally benign reagent and the ease of the reaction operation were particularly attractive, and enabled the controlled oxidation and facile cleavage of acetate in a preceding step. This journal is
- Gurawa, Aakanksha,Kumar, Manoj,Rao, Dodla S.,Kashyap, Sudhir
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supporting information
p. 16702 - 16707
(2020/10/27)
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- Microwave-Assisted Catalytic Acetylation of Alcohols by Gold-Nanoparticle-Supported Gadolinium Complex
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A gold nanoparticle (AuNP)-supported gadolinium complex (RS-Au-L-Gd) catalyst was prepared through simple chelation of GdCl3 to the surface-bound spacer, 1,4,7-tris(carboxymethyl)-10-(11-mercaptoundecyl)-1,4,7,10-tetraazacyclododecane (HSDO3A). This AuNP-supported Gd complex was found to be a highly effective catalyst for the acetylation of various alcohols and phenol in the presence of acetic anhydride. With a loading of 0.4 mol% of RS-Au-L-Gd, the almost complete transformation can be achieved in 60 s under microwave irradiation conditions. This hybrid catalyst was air stable, water soluble, dissolvable in many organic media, and precipitable. It can be readily recycled more than eight times without any significant loss of its catalytic activity. GRAPHICAL ABSTRACT.
- Chang, Tsao-Ching,Yu, Shuchun Joyce
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p. 661 - 672
(2015/10/29)
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- Benzofurans or isochromenes via the ring-opening cyclization of cyclopropene derivatives with organolithiums
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A new and efficient approach to benzocycles from cyclopropene derivatives is described. Deprotection by organolithiums and subsequent ring-opening cyclization of the related 2-cyclopropenyl phenyl or benzyl acetates generated benzofurans and isochromenes in one pot.
- Liu, Yu,Ma, Shengming
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supporting information; experimental part
p. 720 - 723
(2012/04/17)
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- Highly selective one-pot conversion of THP and MOM ethers to acetates by indium triiodide-catalysed deprotection and subsequent transesterification by ethyl acetate
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The chemoselective one-pot conversion of tetrahydropyranyl (THP) and methoxymethyl (MOM) ethers of primary alcohols to the corresponding acetates was presented. It was done using indium triiodide-catalysed deprotection and subsequent acetylation by ethyl acetate through a transesterification process. The advantages offered by the method included operational simplicity, 'green' methodology involving no toxic or hazardous chemicals and high yield.
- Ranu, Brindaban C.,Hajra, Alakananda
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p. 2262 - 2265
(2007/10/03)
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- Synthesis of Novel Phosphorus Heterocycles: 1,3-Dihydro-2,1-Benzoxaphosphole 1-Oxides
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A class of novel phosphorus heterocycles, 1,3-dihydro-2,1-benzoxaphosphole 1-oxides, has been prepared by two different routes.One general approach involves the cyclization of ortho-substituted phenylphosphinic acid derivatives under either thermal or sol
- Miles, J. A.,Grabiak, R. C.,Cummins, C.
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p. 1677 - 1682
(2007/10/02)
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