Pelšs, Andrejs Gandhamsetty, Narasimhulu Smith, James R Mailhol, Damien Silvi, Mattia Watson, Andrew J A Perez-Powell, Isabel Prévost, Sébastien Schützenmeister, Nina Moore, Peter R
...
Published in
Chemistry (Weinheim an der Bergstrasse, Germany)
Re-investigation of the l-proline catalyzed double aldol cascade dimerization of succinaldehyde for the synthesis of a key bicyclic enal intermediate, pertinent in the field of stereoselective prostaglandin synthesis, is reported. The yield of this process has been more than doubled, from 14 % to a 29 % isolated yield on a multi-gram scale (32 % NM...
Lin, Hua Wang, Chao Bannister, Thomas D Kamenecka, Theodore M
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Chemistry (Weinheim an der Bergstrasse, Germany)
The first selective PdII -catalysed γ-C(sp3 )-H and γ-C(sp2 )-H arylation of free amino esters using a commercially available catalytic transient directing group. A variety of free amino esters, including α-amino esters and β-amino esters, amino monoesters and amino bis-esters, are shown to react with a diverse range of simple aryl and heteroaryl i...
Eigler, Siegfried Grimm, Stefan Hirsch, Andreas
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Chemistry (Weinheim an der Bergstrasse, Germany)
In this study, we use our recently prepared graphene oxide (GO) with an almost intact σ-framework of carbon atoms (ai-GO) to probe the thermal stability of the carbon framework for the first time. Ai-GO exhibits few defects because CO2 formation is prevented during synthesis. Ai-GO was thermally treated before chemical reduction and the resulting d...
Rauser, Marian Ascheberg, Christoph Niggemann, Meike
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Chemistry (Weinheim an der Bergstrasse, Germany)
The first general protocol for the direct reductive N-functionalization of aliphatic nitro compounds is presented. The nitro group is partially reduced to a nitrenoid, with a mild and readily available combination of B2 pin2 and zinc organyls. Thereby, the formation of an unstable nitroso intermediate is avoided, which has so far severely limited r...
Frazee, Christopher Burford, Neil McDonald, Robert Ferguson, Michael J Decken, Andreas Patrick, Brian O
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Chemistry (Weinheim an der Bergstrasse, Germany)
Reaction of Ph2 SbCl3 with 2,2'-bipyridine and Me3 SiOSO2 CF3 releases chlorobenzene, which is interpreted as a reductive (SbV /SbIII ) elimination from a complex of a stiboranium cation. Conversely, reactions of Ph2 SbCl3 with 4-methylpyridine-N-oxide and AgOSO2 CF3 give redox-resistant complexes with the generic formulae [Ph2 SbCl3-x Lx+1 ][OTf]x...
Fumagalli, Fernando Warratz, Svenja Zhang, Shou-Kun Rogge, Torben Zhu, Cuiju Stückl, A Claudia Ackermann, Lutz
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Chemistry (Weinheim an der Bergstrasse, Germany)
meta-Selective C-H alkylations of bioactive purine derivatives were accomplished by versatile ruthenium catalysis. Thus, the arene-ligand-free complex [Ru(OAc)2 (PPh3 )2 ] enabled remote C-H functionalizations with ample scope and excellent levels of chemo- and positional selectivities. Detailed experimental and computational mechanistic studies pr...
Hamkalo, Michal Fita, Piotr Fedorynski, Michal Makosza, Mieczyslaw
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Chemistry (Weinheim an der Bergstrasse, Germany)
We present the first unambiguous evidence of the interfacial mechanism of phase-transfer catalysis (PTC) by direct observation of the formation of carbanions in the interfacial region between the aqueous and the organic phase by using a surface-sensitive spectroscopic method known as second harmonic generation (SHG). Ion exchange of carbanions adso...
Geitner, Felix S Wallach, Christoph Fässler, Thomas F
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Chemistry (Weinheim an der Bergstrasse, Germany)
The reaction of [(Ge9 {Si(TMS)3 }2 PtBu2 )]- with NHCMes CuCl yields [(Ge9 {Si(TMS)3 }2 )(tBu2 P)]Cu(NHCMes ) (1), which is a new derivative of the recently reported monomeric zwitterionic tetrel cluster compounds [(Ge9 {Si(TMS)3 }2 )(tBu2 P)]M(NHCDipp ) (M: Cu, Ag, Au). By contrast, the reaction of the same anion [(Ge9 {Si(TMS)3 }2 PtBu2 )]- with ...
Cao, Levy L Bamford, Karlee L Liu, Liu Leo Stephan, Douglas W
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Chemistry (Weinheim an der Bergstrasse, Germany)
Reactions of [Cp*2 Fe] with the Lewis acid [Zn(C6 F5 )2 ] in the presence of [(PhC(S)S)2 ], 9,10-phenanthrenedione or 4,5-pyrenedione yield the salt [Cp*2 Fe][(PhC(S)S)Zn(C6 F5 )2 ] 1, [Cp*2 Fe][((C14 H8 O2 )Zn(C6 F5 )2 )⋅] 4, and [Cp*2 Fe][((C16 H8 O2 )Zn(C6 F5 )2 )⋅] 5, respectively. The latter two species represent the first examples of isolable...
Kondoh, Azusa Terada, Masahiro
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Chemistry (Weinheim an der Bergstrasse, Germany)
A novel "umpolung" intramolecular cyclization of alkynyl imines, in which the electrophilic imine sp2 -carbon formally serves as a nucleophilic site, was developed under Brønsted base catalysis. The reaction involves the unprecedented catalytic generation of α-aminoester enolates from α-iminoesters via the 1,2-addition of the anion of a secondary p...
