92102-13-1

Upstream product

• 78-92-2 iso-butanol 
• 108-67-8 1,3,5-trimethyl-benzene 
• 1912-32-9 n-butyl methanesulfonate 
• 715-11-7 2-tosyloxybutane 
• 88496-88-2 1-methylpropylboronic acid 
• 576-83-0 2,4,6-trimethylphenyl bromide 
• 75618-25-6 butyl triflate 

Downstream Products

• 177969-53-8 3-sec-butyl-2,4,6-trimethylbenzoic acid 

Relevant academic research and scientific papers

Direct functionalization of arenes by primary alcohol sulfonate esters catalyzed by gold(III)

Alkylation of arenes by primary alcohol triflate or methanesulfonate esters can be efficiently catalyzed by AuCl3 with silver triflate. Copyright

Teaching an old carbocation new tricks: Intermolecular C-H insertion reactions of vinyl cations

Vinyl carbocations have been the subject of extensive experimental and theoretical studies over the past five decades. Despite this long history in chemistry, the utility of vinyl cations in chemical synthesis has been limited, with most reactivity studies focusing on solvolysis reactions or intramolecular processes. Here we report synthetic and mechanistic studies of vinyl cations generated through silylium-weakly coordinating anion catalysis. We find that these reactive intermediates undergo mild intermolecular carbon-carbon bond-forming reactions, including carbon-hydrogen (C-H) insertion into unactivated sp3 C-H bonds and reductive Friedel-Crafts reactions with arenes. Moreover, we conducted computational studies of these alkane C-H functionalization reactions and discovered that they proceed through nonclassical, ambimodal transition structures. This reaction manifold provides a framework for the catalytic functionalization of hydrocarbons using simple ketone derivatives.

Efficient synthesis of sterically hindered arenes bearing acyclic secondary alkyl groups by suzuki-miyaura cross-couplings

Bulky P,P-O ligands were designed to inhibit isomerization and reduction side reactions during the cross coupling between sterically hindered aryl halides and alkylboronic acids. Suzuki-Miyaura cross-couplings between di-ortho-substituted aryl bromides and acyclic secondary alkylboronic acids have been achieved with high yields. The method has also enabled the preparation of ortho-alkoxy di-ortho-substituted arenes bearing isopropyl groups in excellent yields. The utility of the synthetic method has been demonstrated in a late-stage modification of estrone and in the application to a new synthetic route toward gossypol. No side reaction: The shown bulky P,P-O ligands (right) successfully inhibit isomerization and reduction side reactions of the cross-coupling of sterically hindered substrates such as di-ortho-substituted aryl bromides with acyclic secondary alkylboronic acids. The method also allows the preparation of ortho-alkoxy di-ortho-substituted isopropyl arenes in excellent yields.

Process for the preparation of alkylated aromatic carboxylic acids and acyl halides

The invention relates to a process for the preparation of polyalkylated aromatic carboxylic acids of formula I STR1 wherein R1, R2, R3, R4 and R5 are each independently of one another hydrogen, C1 -C20 alkyl, halogen or C5 -C8 cycloalkyl, with the proviso that at least two of the substituents R1, R2, R3, R4 or R5 are alkyl and/or cycloalkyl, by reacting corresponding aromatic hydrocarbons with carbon dioxide, which reaction is carried out observing special ratios of temperature and pressure. The invention furthermore relates to a one-pot process for the preparation of the corresponding acyl halides.