On the Origin of the Non-Planarity in Biarylsilyloxonium Ions
The structure determination of a series of biphenylsilyloxonium cations through NMR and XRD studies, supported by DFT calculations was carried out, allowing to get insights into the origin of the oxygen pyramidalization in biphenyl and binaphthylsilyl oxoniums. Low barrier of inversion in the oxygenyl series points toward a key role of the biaryl axis in the inversion of configuration at the oxygen center.
Fernandes, Anthony J.,Robert, Frederic,Landais, Yannick,Künzler, Sandra,Müller, Thomas
supporting information
p. 15496 - 15500
(2021/10/07)
Arenediazonium Tosylates (ADTs) as Efficient Reagents for Suzuki-Miyaura Cross-Coupling in Neat Water
A simple, convenient, and environment-friendly procedure for the preparation of substituted biaryls via Suzuki-Miyaura cross-coupling- was developed. The use of arenediazonium tosylates and corresponding boron compounds allows a conversion in neat water in the presence of commercially available Pd(OAc)2 under mild conditions with tolerance to a wide range of functional groups. A procedure particularly useful for the synthesis of di-ortho-substituted biaryls was developed.
Kutonova, Ksenia V.,Jung, Nicole,Trusova, Marina E.,Filimonov, Victor D.,Postnikov, Pavel S.,Br?se, Stefan
A novel and efficient Pd-catalyzed C-H acetoxylation is described. The approach uses R2(O)P as a directing group to synthesize various substituted 2′-phosphorylbiphenyl-2-OAc compounds. Notably, the reaction exhibits smooth operation under mild conditions and shows good functional group tolerance. Products are obtained with high selectivity and yields. This journal is the Partner Organisations 2014.
Soft propargylic deprotonation: Designed ligand enables au-catalyzed isomerization of alkynes to 1,3-Dienes
By functionalizing the privileged biphenyl-2-ylphosphine with a basic amino group at the rarely explored 3′ position, the derived gold(I) complex possesses orthogonally positioned "push" and "pull" forces, which enable for the first time soft propargylic deprotonation and permit the bridging of a difference of >26 pKa units (in DMSO) between a propargylic hydrogen and a protonated tertiary aniline. The application of this design led to efficient isomerization of alkynes into versatile 1,3-dienes with synthetically useful scope under mild reaction conditions.
Wang, Zhixun,Wang, Yanzhao,Zhang, Liming
supporting information
p. 8887 - 8890
(2014/07/08)
Rhodium-catalyzed asymmetric synthesis of silicon-stereogenic dibenzooxasilines via enantioselective transmetalation
A rhodium-catalyzed asymmetric synthesis of silicon-stereogenic dibenzooxasilines has been developed. High enantioselectivities have been achieved by employing (S,S)-Me-Duphos as the ligand through " enantioselective transmetalation".
Rhodium-catalyzed asymmetric synthesis of silicon-stereogenic dibenzooxasilines via enantioselective transmetalation
A rhodium-catalyzed asymmetric synthesis of silicon-stereogenic dibenzooxasilines has been developed. High enantioselectivities have been achieved by employing (S,S)-Me-Duphos as the ligand through " enantioselective transmetalation".
Achieving conformational control over C-C, C-N and C-O bonds in biaryls, N,N′-diarylureas and diaryl ethers: Advantages of a relay axis
The orientation of Ar-C, Ar-N and Ar-O bonds in biaryls, N,N′-diarylureas and diaryl ethers (whose conformers are distinguishable by NMR) may be controlled with a selectivity up to >95: 5 by an adjacent stereogenic centre; the selectivity may be greater when a second stereogenic axis is inserted between the controlling centre and the slowly rotating bond. The Royal Society of Chemistry.
Betson, Mark S.,Bracegirdle, Ann,Clayden, Jonathan,Helliwell, Madeleine,Lund, Andrew,Pickworth, Mark,Snape, Timothy J.,Worrall, Christopher P.
p. 754 - 756
(2007/10/03)
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