6783-05-7 Usage
Description
E-PHENYLETHENYLBORONIC ACID is an organic compound that serves as a versatile reagent in various chemical reactions and synthesis processes. It is particularly useful in the field of organic chemistry for its ability to participate in a range of catalytic reactions, including palladium-catalyzed Suzuki-Miyaura coupling, rhodium-catalyzed intramolecular amination, and iridium-catalyzed addition reactions.
Uses
Used in Chemical Synthesis:
E-PHENYLETHENYLBORONIC ACID is used as a reagent for palladium (Pd)-catalyzed Suzuki-Miyaura coupling reactions, which are widely employed in the synthesis of complex organic molecules, including pharmaceuticals and agrochemicals.
Used in Pharmaceutical Industry:
E-PHENYLETHENYLBORONIC ACID is used as a reagent for rhodium (Rh)-catalyzed intramolecular amination of aryl azides, a process that is crucial in the synthesis of various pharmaceutical compounds.
Used in Organic Chemistry Research:
E-PHENYLETHENYLBORONIC ACID is used as a reagent in diastereoselective synthesis via Pd-catalyzed Heck-Suzuki cascade reaction, which is an important method for constructing complex molecular structures with specific stereochemistry.
Used in Material Science:
E-PHENYLETHENYLBORONIC ACID is used as a reagent in copper (Cu)-mediated cyanation, a process that is essential for the synthesis of various functional materials and polymers.
Used in Asymmetric Synthesis:
E-PHENYLETHENYLBORONIC ACID is used as a reagent for rhodium (Rh)-catalyzed asymmetric addition, a key technique in the preparation of enantiomerically pure compounds, which are important in the pharmaceutical and agrochemical industries.
Used in Catalyst Development:
E-PHENYLETHENYLBORONIC ACID is used as a reagent in diastereoselective synthesis via iridium (Ir)-catalyzed addition, which is a valuable method for the development of new catalysts and catalytic processes.
Used in Cascade Cyclization:
E-PHENYLETHENYLBORONIC ACID is used as a reagent in palladium (Pd)-catalyzed cascade cyclization, a powerful strategy for the construction of complex molecular architectures in a single operation.
Used in Preparation of Optically Active Compounds:
E-PHENYLETHENYLBORONIC ACID is used as a reagent in the preparation of optically active unsaturated amino acids by diastereoselective Petasis borono-Mannich reaction, which is an important method for the synthesis of biologically active molecules.
Used in Synthesis of Amino Alcohol Dienes:
E-PHENYLETHENYLBORONIC ACID is used as a reagent in the preparation of amino alcohol dienes via Petasis 3-component reaction using Ru-catalyzed ring-closing metathesis and isomerization, a process that is essential for the synthesis of complex organic molecules with potential applications in various industries.
Check Digit Verification of cas no
The CAS Registry Mumber 6783-05-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,7,8 and 3 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 6783-05:
(6*6)+(5*7)+(4*8)+(3*3)+(2*0)+(1*5)=117
117 % 10 = 7
So 6783-05-7 is a valid CAS Registry Number.
6783-05-7Relevant articles and documents
Cu-catalyzed [2 + 2 + 1] cascade annulation of vinyl iodonium salts with elemental sulfur/selenium for the modular synthesis of thiophenes and selenophenes
Chen, Chao,Wang, Fei,Wu, Chao,Wu, Yaxing
supporting information, p. 945 - 949 (2022/02/01)
A [2 + 2 + 1] annulation protocol has been established for the modular synthesis of 2,4-disubstituted thiophenes/selenophenes, with excellent regioselectivity. The reactions have been catalyzed by copper salt with elemental sulfur and selenium serving as
Rate dependence on inductive and resonance effects for the organocatalyzed enantioselective conjugate addition of alkenyl and alkynyl boronic acids to β-indolyl enones and β-pyrrolyl enones
Boylan, Amy,Li, Jian-Yuan,Lundy, Brian J.,May, Jeremy A.,Nguyen, Thien S.,Sundstrom, Sasha,Vallakati, Ravikrishna
, (2021/06/16)
Two key factors bear on reaction rates for the conjugate addition of alkenyl boronic acids to heteroaryl-appended enones: the proximity of inductively electron-withdrawing heteroatoms to the site of bond formation and the resonance contribution of available heteroatom lone pairs to stabilize the developing positive charge at the enone β-position. For the former, the closer the heteroatom is to the enone β-carbon, the faster the reaction. For the latter, greater resonance stabilization of the benzylic cationic charge accelerates the reaction. Thus, reaction rates are increased by the closer proximity of inductive electron-withdrawing elements, but if resonance effects are involved, then increased rates are observed with electron-donating ability. Evidence for these trends in isomeric substrates is presented, and the application of these insights has allowed for reaction conditions that provide improved reactivity with previously problematic substrates.
Transition-Metal-Free C(sp2)–C(sp2) Cross-Coupling of Diazo Quinones with Catechol Boronic Esters
Che, Chi-Ming,Wu, Kai,Wu, Liang-Liang,Zhou, Cong-Ying
supporting information, p. 16202 - 16208 (2020/07/17)
A transition-metal-free C(sp2)?C(sp2) bond formation reaction by the cross-coupling of diazo quinones with catechol boronic esters was developed. With this protocol, a variety of biaryls and alkenyl phenols were obtained in good to high yields under mild conditions. The reaction tolerates various functionalities and is applicable to the derivatization of pharmaceuticals and natural products. The synthetic utility of the method was demonstrated by the short synthesis of multi-substituted triphenylenes and three bioactive natural products, honokiol, moracin M, and stemofuran A. Mechanistic studies and density functional theory (DFT) calculations revealed that the reaction involves attack of the boronic ester by a singlet quinone carbene followed by a 1,2-rearrangement through a stepwise mechanism.
