127595-53-3Relevant academic research and scientific papers
Bulky N-Heterocyclic-Carbene-Coordinated Palladium Catalysts for 1,2-Addition of Arylboron Compounds to Carbonyl Compounds
Okuda, Yuta,Nagaoka, Masahiro,Yamamoto, Tetsuya
, p. 6291 - 6300 (2020/11/30)
The synthesis of primary, secondary, and tertiary alcohols by the 1,2-addition of arylboronic acids or boronates to carbonyl compounds, including unactivated ketones, using novel bulky yet flexible N-heterocyclic carbene (NHC)-coordinated 2,6-di(pentan-3-yl)aniline (IPent)-based cyclometallated palladium complexes (CYPs) as catalysts is reported. The PhS-IPent-CYP-catalyzed reactions are efficient at low catalyst loadings (0.02–0.3 mol% Pd), and the exceptional catalytic activity for 1,2-addition is attributed to the steric bulk of the NHC ligand. These reactions can yield a wide range of functionalized benzylic alcohols that are difficult to synthesize by classical protocols using highly active organomagnesium or lithium reagents.
Palladium-catalyzed 1,2-addition of potassium aryl- and alkenyltrifluoroborates to aldehydes using thioether-imidazolinium carbene ligands
Kuriyama, Masami,Shimazawa, Rumiko,Enomoto, Terumichi,Shirai, Ryuichi
, p. 6939 - 6942 (2008/12/22)
(Chemical Equation Presented) Palladium-catalyzed 1,2-addition of potassium aryl- and alkenyltrifluoroborates to aldehydes using thioether- imidazolinium carbene ligands proceeded readily under aqueous conditions. This process tolerated a diverse range of potassium trifluoroborate salts and aldehydes, giving a variety of carbinol derivatives with good to excellent yields.
Efficient 1,2-addition of aryl- and alkenylboronic acids to aldehydes catalyzed by the palladium/thioether-imidazolinium chloride system
Kuriyama, Masami,Shimazawa, Rumiko,Shirai, Ryuichi
, p. 1597 - 1600 (2008/09/17)
(Chemical Equation Presented) The high level of catalyst performance was attainable in the palladium-catalyzed 1,2-addition of aryl-, heteroaryl-, and alkenylboronic acids to aromatic, heteroaromatic, and aliphatic aldehydes using thioether-imidazolinium chloride L5 as a heterobidentate carbene ligand precursor.
Benzofuran derivatives as ET(A)-selective, non-peptide endothelin antagonists
Kaltenbronn,Quin III,Reisdorph,Klutchko,Reynolds,Welch,Flynn,Doherty
, p. 425 - 431 (2007/10/03)
The synthesis and SAR relationships of a series of 4-benzyloxy-3-methylbenzofuran-2-carboxylic acids are described. Compounds from this series show 2- to 16-fold selective binding to the ET(A) receptor in the micromolar range, and two compounds from this series (32 and 40) were demonstrated to exhibit ET(A) antagonist activity.
Regioselective Reductive Electrophilic Substitution of 1,2,3-Trimethoxybenzene and Its 5-Alkyl-Substituted Homologues
Azzena, Ugo,Denurra, Teresa,Melloni, Giovanni,Piroddi, Anna Maria
, p. 5386 - 5390 (2007/10/02)
The methoxy group in the 2-position of 1,2,3-trimethoxybenzene (1) can be regioselectively removed by electron transfer from alkali metals and replaced with a variety of electrophiles in a one-pot procedure, affording 2-substituted resorcinol dimethyl ethers.The usefulness of this synthetic method is illustrated by numerous examples.This reaction procedure has been successfully extended to the 5-methyl-substituted homologue (2), but limitations occur with the higher homologue 1-pentyl-3,4,5-trimethoxybenzene (3).Investigations on the mechanism of demethoxylation, with the aid of labeling experiments, provided clear evidence for the intermediacy of aryl radicals and explained the low yields obtained in the reductive electrophilic substitution of compound 3.
