70260-27-4Relevant articles and documents
Efficient synthetic method of β-fluorocinnamate by arylboronic acids and ethyl 3,3,3-trifluoropropionate under palladium-catalyzed conditions
Chen, Wei-Hao,Pei, Xiao-Jun,Li, Xiao-Xuan,Feng, Yi-Si
, p. 3212 - 3220 (2020)
A convenient and efficient method for synthesizing β-fluorocinnamate and derivatives is reported. Palladium (II) catalysis was employed in β-F elimination and coupling reaction of phenylboronic acid and ethyl 3,3,3-trifluoropropionate with a high yield and E-selectivity. The reaction was conducted under mild conditions and could be widely adapted to boronic acid substrates.
A Bio-Inspired, Catalytic e → Z Isomerization of Activated Olefins
Metternich, Jan B.,Gilmour, Ryan
, p. 11254 - 11257 (2015/09/21)
Herein, Natures flavin-mediated activation of complex (poly)enes has been translated to a small molecule paradigm culminating in a highly (Z)-selective, catalytic isomerization of activated olefins using (-)-riboflavin (up to 99:1 Z/E). In contrast to the prominent Z → E isomerization of the natural system, it was possible to invert the directionality of the isomerization (E → Z) by simultaneously truncating the retinal scaffold, and introducing a third olefin substituent to augment A1,3-strain upon isomerization. Consequently, conjugation is reduced in the product chromophore leading to a substrate/product combination with discrete photophysical signatures. The operationally simple isomerization protocol has been applied to a variety of enone-derived substrates and showcased in the preparation of the medically relevant 4-substituted coumarin scaffold. A correlation of sensitizer triplet energy (ET) and reaction efficiency, together with the study of additive effects and mechanistic probes, is consistent with a triplet energy transfer mechanism.
