83465-27-4

Upstream product

• 119-67-5 o-carboxybenzaldehyde 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 65-85-0 benzoic acid 
• 140-88-5 ethyl acrylate 
• 14078-85-4 1-methyl-2-carboxy-1,2-dicarba-closo-dodecaborane⁽¹²⁾ 
• 100-52-7 benzaldehyde 
• 62573-86-8 N-benzoylbenzimidazole 
• 40138-16-7 2-formylbenzene boronic acid 
• 6630-33-7 ortho-bromobenzaldehyde 
• 1345714-85-3 (Z)-ethyl 3-(2-formylphenyl)acrylate 
• 86867-62-1 (E)-3-(2-formylphenyl)propenoic acid ethyl ester 
• 86905-48-8 Bromo-(3-oxo-1,3-dihydro-isobenzofuran-1-yl)-acetic acid ethyl ester 
• 64-17-5 ethanol 
• 201230-82-2 carbon monoxide 

Downstream Products

• 18454-53-0 (E)-o-carboxycinnamic acid 

Relevant academic research and scientific papers

One-Pot Process to Carborano-Coumarin via Catalytic CascadeDehydrogenative Cross-Coupling

Ir-catalyzed cascade dehydrogenative CH/BH and BH/OH cross-coupling of carboranyl carboxylic acid with readily available benzoic acid has been achieved, leading to the facile synthesis of previously unavailable carborano-coumarin in a simple one-pot process. Two cage B—H, one aryl C—H and one O—H bonds are activated to construct efficiently new B—C and B—O bonds. The cascade cyclization can stop at the first B—H/C—H cross-coupling step by tuning the reaction conditions, resulting in a series of α-carboranyl benzoic acid and aryl carborane derivatives. Control experiments indicate that B—H/C—H dehydrocoupling proceeds preferentially over B—H/O—H dehydrocoupling, and both directing groups and oxidants are crucial for this reaction. An iridium(V) intermediate is proposed to be involved in the catalytic cycle.

Urea-Substituted Tetramethylcyclopentadienyl Ligands for Supramolecularly Accelerated RhIII-Catalyzed ortho-C?H Olefination of Benzoic Acid Derivatives

The design and synthesis of air-stable and conveniently crystallizable RhIII-cyclopentadienyl catalysts substituted with a urea moiety, which are able to accelerate the C?H olefination of benzoic acid derivatives, is reported. Through kinetic s

RhIII-Catalyzed Regioselective Synthesis of Phthalides with Water as the Solvent

Under rhodium(III)-catalyzed conditions, a broad range of benzoic acids reacted with acrylates successfully to provide phthalides through the direct functionalization of a C–H bond followed by β-hydride elimination and intramolecular Michael addition. The reaction provides an alternative strategy for the construction of diverse and useful phthalide derivatives from readily available starting materials. In most cases, high regioselectivity was obtained, and this is the first report of the rhodium-catalyzed synthesis of phthalides in water.

One-Pot Sequential N-Heterocyclic Carbene/Rhodium(III) Catalysis: Synthesis of Fused Polycyclic Isocoumarins

A one-pot sequential N-heterocyclic carbene–rhodium (NHC-Rh) catalysis is described, demonstrating the compatibility of NHC and Rh catalysts. N-Heterocyclic carbene-catalyzed aerobic oxidation of benzaldehydes and subsequent rhodium(III)-catalyzed oxidative coupling/annulation with multiple bonds enabled the formation of two C–O bonds and one C–C bond in a single pot. This operationally easy, one-pot protocol under air provides access to a diverse array of valuable fused polycyclic isocoumarins. (Figure presented.).

Synthesis of Phthalides through Tandem Rhodium-Catalyzed C–H Olefination and Annulation of Benzamides

The rhodium(III)-catalyzed tandem C–H olefination and cyclization of benzamides with various alkenes is described. This protocol provides direct access to highly substituted phthalides, which are known as crucial frameworks of biologically active compounds. In particular, the amide directing group containing a benzimidazole group facilitates the activation of aromatic ortho-C–H bonds leading to olefination intermediates, and is spantaneously converted into an acid moiety, which can further undergo the intramolecular annulation process.

Cu-MEDIATED ANNULATION FOR THE EFFECTIVE SYNTHESIS OF 3-SUBSTITUTED PHTHALIDES

The present invention disclosed herein is a novel commercially feasible, one pot synthesis of library of 3-substituted phthalides of formula I via CuCN mediated oxidative cyclization in high yield. Formula I

NHC-catalyzed oxidative cyclization reaction for the synthesis of 3-substituted phthalides

An efficient NHC-catalyzed domino oxidation/oxa-Michael addition reaction of 2-alkenylbenzaldehydes has been developed to afford 3-substituted phthalides bearing a C3-stereogenic center with a broad substrate scope and wide functional group tolerance. The preliminary results of the asymmetric process have been provided as well. the Partner Organisations 2014.

Cu-MEDIATED ANNULATION FOR THE EFFECTIVE SYNTHESIS OF 3-SUBSTITUTED PHTHALIDES

The present invention disclosed herein is a novel commercially feasible, one pot synthesis of library of 3-substituted phthalides of formula I via CuCN mediated oxidative cyclization in high yield. Formula I

A Facile Synthesis of 3-Substituted Phthalides

1(3H)-Isobenzofuranone (phthalides) and its derivatives possess a wide range of biological activities. A new method was found for the synthesis of 3-substituted phthalides featured with the convenient condensation reaction of 3-ethoxyphthalide with carbanions in high yields.

Palladium-catalyzed synthesis of 3-alkylphthalides via carbonylative cyclization of o-bromobenzaldehyde with 1,3-dicarbonyl compounds

o-Bromobenzaldehyde reacts with 1,3-dicarbonyl compounds under carbon monoxide in the presence of a catalytic amount of PdCl2(PPh3)2 to give the corresponding 3-alkylphthalides in moderate to good yields.