18019-56-2

Upstream product

• 98-86-2 acetophenone 
• 110349-26-3 tert-butyl 2-iodobenzoate 
• 124-38-9 carbon dioxide 
• 24892-82-8 1-bromo-2-(1-phenylpropen-1-yl)benzene 
• 57271-91-7 N-butyl-2-hydroxybenzamide 
• 119-36-8 methyl salicylate 
• 108-86-1 bromobenzene 
• 599-67-7 1,1-diphenylethanol 
• 93898-92-1 2-(1-phenylethyl)benzoic acid 
• 612-35-1 2-Benzylbenzoic acid 
• 50-00-0 formaldehyd 
• 82645-13-4 1-(2-bromophenyl)-1-phenylethan-1-ol 
• 1242592-42-2 (E)-1,3-dihydro-3-methyl-3-phenyl-1-(phenylimino)isobenzofuran 
• 577-56-0 2-acetyl-benzoic acid 

Downstream Products

• 6637-53-2 3-hydroxy-3-phenyl-2,3-dihydro-isoindol-1-one 
• 19571-30-3 4-phenylisoquinoline 
• 65810-96-0 1-chloro-4-phenyl-isoquinoline 
• 112224-35-8 3-chloro-2,4-diphenyl-3,4-dihydro-2H-isoquinolin-1-one 
• 6621-97-2 3-hydroxy-2,3-diphenyl-1-isoindolinone 
• 77894-41-8 2,4-diphenylisoquinolin-1(2H)-one 
• 36828-24-7 4-phenyl-isoquinolin-1-ol 
• 93898-92-1 2-(1-phenylethyl)benzoic acid 
• 110474-85-6 2-(2-chloro-1-phenyl-vinyl)-benzoic acid anilide 
• 17582-84-2 2-(1-phenylethenyl)benzoic acid 

Relevant academic research and scientific papers

Access to Diarylmethanols by Wittig Rearrangement of ortho-, meta-, and para-Benzyloxy- N-Butylbenzamides

The N-butyl amide group, CONHBu, has been found to be an effective promoter of the [1,2]-Wittig rearrangement of aryl benzyl ethers and thus allow the two-step synthesis of isomerically pure substituted diarylmethanols starting from simple hydroxybenzoic acid derivatives. The method is compatible with a wide range of functional groups including methyl, methoxy, and fluoro, although not with nitro and, unexpectedly, is applicable to meta as well as ortho and para isomeric series.

Base-Directed Photoredox Activation of C-H Bonds by PCET

Photoredox catalysis using proton-coupled electron transfer (PCET) has emerged as a powerful method for bond transformations. We previously employed traditional chemical oxidants to achieve multiple-site concerted proton-electron transfer (MS-CPET) activation of a C-H bond in a proof-of-concept fluorenyl-benzoate substrate. As described here, photoredox oxidation of the fluorenyl-benzoate follows the same rate constant vs driving force trend determined for thermal MS-CPET. Analogous photoredox catalysis enables C-H activation and H/D exchange in a number of additional substrates with favorably positioned bases. Mechanistic studies support our hypothesis that MS-CPET is a viable pathway for bond activation for substrates in which the C-H bond is weak, while stepwise carboxylate oxidation and hydrogen atom transfer likely predominate for stronger C-H bonds.

Catalytic Lactonization of Unactivated Aryl C-H Bonds with CO2: Experimental and Computational Investigation

The first catalytic lactonization of unactivated aryl C-H bonds with CO2 to afford important phthalides is reported. Notably, this method features high selectivity, excellent functional group tolerance, smooth scalability, and facile product diversification. DFT calculations reveal that a novel insertion of two CO2 into the O-Pd bond of a palladacycle might be the key step, providing great potential and a different perspective for carbonylation with CO2.

Scalable Electrochemical Dehydrogenative Lactonization of C(sp2/sp3)-H Bonds

A practical, electrochemical method is developed for the direct dehydrogenative lactonization of C(sp2/sp3)-H bonds under external oxidant- and metal-free conditions, delivering diverse lactones, including coumarin derivatives with excellent regioselectivity. The scalable nature of this newly developed electrochemical process was demonstrated on a 40 g scale following an operationally simple protocol. The remote lactonization of C(sp3)-H bonds would constitute an important synthetic advance toward electrochemical C-O bond formation.

Domino [Pd]-Catalysis: One-Pot Synthesis of Isobenzofuran-1(3H)-ones

An efficient domino [Pd]-catalysis for the synthesis of isobenzofuran-1(3H)-ones is presented. The strategy shows broad substrate scope and is amenable to o-bromobenzyl tertiary/secondary/primary alcohols. Significantly, the method was applied to the synthesis of antiplatelet drug n-butyl phthalide and cytotoxic agonist 3a-[4′-methoxylbenzyl]-5,7-dimethoxyphthalide.

Domino One-Pot Process for the Synthesis of Isobenzofuran-1(3 H)-ones via [Cu]-Catalysis Using Water as the Green Solvent

An efficient domino one-pot strategy via [Cu]-catalyzed intermolecular "cyanation" of o-bromobenzyl alcohols → in situ intramolecular "nucleophilic attack" → "hydrolysis" is presented, for the synthesis of isobenzofuran-1(3H)-ones. Significantly, the reaction is successfully carried out under environmentally benign conditions, using water as sole green solvent.

New, facile synthesis of 3,3-disubstituted phthalides based on the reaction of α-substituted 2-lithiostyrenes with carbon dioxide

A new method to prepare 3,3-disubstituted phthalides [isobenzofuran-1(3H)-ones] from α-substituted 2-bromostyrenes has been developed. The reaction of α-substituted 2-lithiostyrenes, generated in situ by bromine-lithium exchange between α-substituted 2-bromostyrenes and butyllithium, with carbon dioxide gave the corresponding lithium 2-vinylbenzoates, which upon treatment with concentrated hydrochloric acid afforded the desired products in one pot.

Hydriodic acid-mediated cyclization of a-substituted secondary 2-ethenylbenzamides: Synthesis of 2-substituted 2,3-dihydro-3,3-dimethyl-1H- isoindol-1-ones and 3,3-disubstituted (E)-1-(arylimino)-1,3- dihydroisobenzofurans

A new and facile method for the preparation of 2-substituted 2,3-dihydro-3,3-dimethyl-1H-isoindol-1-ones 3 and 3,3-disubstituted (E)-1-(arylimino)-1,3-dihydroisobenzofurans 6 has been developed. Thus, treatment of N-alkyl(or aryl)-2-(1-methylethen-1-yl)be

Mesityllithium as a reagent for chemoselective halogen-lithium exchange reaction.

[figure: see text] Mesityllithium was found to be an excellent selective lithiating agent to prepare aryllithium compounds having alkoxycarbonyl groups. To extend our studies on chemoselective lithiation, an important precursor for the synthesis of camptothecin was prepared using a halogen-lithium exchange reaction followed by an intramolecular 1,2-addition.