153227-31-7

Upstream product

• 189099-57-8 1-bromo-4-[2-(4-methoxyphenyl)ethynyl]benzene 
• 1122-91-4 4-bromo-benzaldehyde 
• 849590-39-2 (±)-N-(4-methoxybenzylidene)-2-methylpropane-2-sulfinamide 
• 26167-16-8 [(4-bromophenyl)methylene]bis(trimethylsilane) 
• 123-11-5 4-methoxy-benzaldehyde 
• 51044-13-4 4-bromobenzyl triphenylphosphonium bromide 

Relevant academic research and scientific papers

E, Z -Selectivity in the reductive cross-coupling of two benzaldehydes to stilbenes under substrate control

Unsymmetrical E- and Z-stilbenes can be synthesized from two differently substituted benzaldehydes in a MesP(TMS)Li-promoted reductive coupling sequence. Depending on the order of addition of the two coupling partners, the same olefin can be produced in either E- or Z-enriched form under identical reaction conditions. A systematic study of the correlation between the stereochemical outcome of the reaction and the substitution pattern at the two aldehydes is presented. The results can be used as guidelines to predict the product stereochemistry. This journal is

Z-Stereoselective Aza-Peterson Olefinations with Bis(trimethylsilane) Reagents and Sulfinyl Imines

Highly stereoselective aza-Peterson olefinations from bench-stable α,α-bis(trimethylsilyl)toluene reagents and N-substituted imines have been achieved using TMSO-/Bu4N+ as Lewis base activator in THF. Remarkably, and for the first time, N-t-butanesulfinyl imines were utilized for the synthesis of Z-stilbenes with excellent selectivities, while N-aryl imines generated E-stilbenes under identical reaction conditions. The protocol proved general for numerous examples with low molecular weight byproducts formed. The origin of the Z-selectivity is proposed to be a result of diastereoselective addition to N-t-butanesulfinyl imines followed by syn-elimination of an in situ formed hypervalent silicate.

1-(α-Aminobenzyl)-2-naphthol as phosphine-free ligand for Pd-catalyzed Suzuki and one-pot Wittig-Suzuki reaction

Air stable and easily accessible, 1-(α-aminobenzyl)-2-naphthols are used as efficient phosphine-free ligands in palladium-catalyzed Suzuki reaction for a variety of substrates under conventional heating as well as ultrasonic conditions. Multi-brominated aromatic substrates were successfully converted to corresponding arylated moieties with good conversion and selectivity. A novel one-pot two-step cascade reaction strategy involving Wittig and Suzuki reactions is developed for efficient synthesis of 4-styryl biphenyls (C 6-C2-C6-C6 unit). Copyright 2012 John Wiley & Sons, Ltd. Phosphine free 1-(α-aminobenzyl)-2- naphthol ligands are used for Pd catalyzed Suzuki and one-pot Wittig-Suzuki reaction to efficiently prepare styryl biphenyls (C6-C 2-C6-C6 unit). Copyright

One-pot hydrosilylation-protodesilylation of functionalized diarylalkynes: a highly selective access to Z-stilbenes. Application to the synthesis of combretastatin A-4

An efficient stereoselective synthesis of Z-stilbenes has been developed from diarylalkynes via a new hydrosilylation-protodesilylation process. The scope and limitation of this method is presented to stereoselectively prepare a wide range of (Z)-stilbenes in a one-pot way is presented. A concise application to the preparation of combretastatin A-4 (CA-4), a vascular targeting agent inhibitor of tubulin polymerisation is described.