183140-16-1

Upstream product

• 18052-27-2 tert-butyldimethyl(phenoxy)silane 
• 140-88-5 ethyl acrylate 
• 123-08-0 4-hydroxy-benzaldehyde 
• 120743-99-9 p-[(tert-butyldimethylsilyl)oxy]benzaldehyde 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 1202785-08-7 C₂₈H₃₇F₃O₄Si 
• 1303501-13-4 1,9-bis(4-hydroxyphenyl)-3,7-dihydroxynonan-5-one 
• 522602-18-2 ethyl 3-(4-((tert-butyl(dimethyl)silyl)oxy)phenyl)propanoate 
• 1421598-67-5 (+)-(3S,7S)-1,9-bis(4-(tert-butyldimethylsilyloxy)phenyl)-3,7-dihydroxynonan-5-one 
• 147974-20-7 3-[4-(tert-butyl-dimethyl-silanyloxy)phenyl]propionaldehyde 
• 622397-33-5 (S)-1-(4-((tert-butyldimethylsilyl)oxy)phenyl)hex-5-en-3-ol 
• 1421598-63-1 C₂₆H₃₈O₃Si 
• 1421598-64-2 C₂₆H₃₈O₄Si 
• 1421598-65-3 C₄₁H₆₂O₆Si₂ 

Relevant academic research and scientific papers

Enantioselective total synthesis of (-)-ericanone

The first total synthesis of (-)-ericanone was achieved in 10 steps with a 16% overall yield from p-hydroxybenzaldehyde. Notable features of this stereocontrolled approach include a Keck allylation to install the stereocenter at C3 and a 1,5-anti aldol reaction to install the hydroxyl group at C7.

Ligand-accelerated non-directed C-H functionalization of arenes

The directed activation of carbon-hydrogen bonds (C-H) is important in the development of synthetically useful reactions, owing to the proximity-induced reactivity and selectivity that is enabled by coordinating functional groups. Palladium-catalysed non-directed C-H activation could potentially enable further useful reactions, because it can reach more distant sites and be applied to substrates that do not contain appropriate directing groups; however, its development has faced substantial challenges associated with the lack of sufficiently active palladium catalysts. Currently used palladium catalysts are reactive only with electron-rich arenes, unless an excess of arene is used, which limits synthetic applications. Here we report a 2-pyridone ligand that binds to palladium and accelerates non-directed C-H functionalization with arene as the limiting reagent. This protocol is compatible with a broad range of aromatic substrates and we demonstrate direct functionalization of advanced synthetic intermediates, drug molecules and natural products that cannot be used in excessive quantities. We also developed C-H olefination and carboxylation protocols, demonstrating the applicability of our methodology to other transformations. The site selectivity in these transformations is governed by a combination of steric and electronic effects, with the pyridone ligand enhancing the influence of sterics on the selectivity, thus providing complementary selectivity to directed C-H functionalization.