29886-65-5Relevant articles and documents
Photo-Fries reaction in acetoxyphenyl thiophenes
Benassi, Enrico,Bertarelli, Chiara,Bianco, Andrea,Galli, Paola,Moretti, Paola,Ortica, Fausto
, (2020)
Two new acetoxyphenyl thiophenes with different conjugation length and undergoing the photo-Fries reaction upon exposure to UV light are presented. These molecules have been characterized in solution by means of different spectroscopic techniques in order to study the evolution and selectivity of the photo-induced reaction. During such a reaction, isosbestic points appear in the UV–vis spectra, indicating a good selectivity of the reaction for both the derivatives. By means of IR measurements, we follow the reaction and determine the kinetics and the quantum yield. The photoproducts are isolated by HPLC and characterized by 1H-NMR whose results confirm the formation of the ortho derivative as the most probable one and we estimate the degree of conversion of the reaction. High-level quantum mechanical calculations both in gas and solvated phase are employed to strongly support the interpretation of the experimental results, and assess the reaction product.
A Series of 2,5-Bis(5-aryl-2-thienyl)pyrazines with a Linear-Shaped (D-π)2-A System: Synthesis and study of the optical properties including fluorosolvatochromism and proton-base-sensing
Muraoka, Hiroki,Iwabuchi, Naoki,Ogawa, Satoshi
, p. 1358 - 1369 (2019/09/18)
A series of 2,5-bis(5-aryl-2-thienyl)pyrazines with distinct optical properties tuned by the intramolecular charge transfer (ICT) degree based on the donor strength of the aryl groups have been synthesized. It was found that 2,5-bis[5-(4-N,N-dibutyl-amino
An efficient protocol for the palladium-catalysed Suzuki-Miyaura cross-coupling
Marziale, Alexander N.,Jantke, Dominik,Faul, Stefan H.,Reiner, Thomas,Herdtweck, Eberhardt,Eppinger, Joerg
supporting information; experimental part, p. 169 - 177 (2011/03/23)
The palladacyclic catalyst precursor received by ortho-palladation of ([1,1′-biphenyl]-2-yloxy)diisopropyl-phosphine represents a highly active system for Suzuki-Miyaura cross-coupling reactions when used in neat water. An efficient, broadly applicable and sustainable aqueous protocol was developed using 2.5 eq. of Na2CO3 as base, allowing the reaction to be performed under air and at ambient temperature with Pd loadings of 0.04 mol%. Coupling products are obtained in high yields and excellent purity by simple filtration with no organic solvents needed throughout the whole reaction. A broad variety of functional groups are tolerated and a large number of substrates can be applied with this protocol. The crystal structure of the palladacyclic catalyst precursor is presented as well as investigations targeting the nature of catalyst activation and the active catalytic species.
