1344667-71-5Relevant articles and documents
Carboxylate-directed C-H allylation with allyl alcohols or ethers
Hu, Xiao-Qiang,Hu, Zhiyong,Trita, A. Stefania,Zhang, Guodong,Goo?en, Lukas J.
, p. 5289 - 5294 (2018)
A [Ru(p-cymene)Cl2]2 catalyst activates allyl alcohols and ethers for the regioselective ortho-C-H allylation of aromatic and heteroaromatic carboxylates. The reaction is orthogonal to most C-H functionalisations with allyl alcohols in that allyl arenes rather than carbonyl compounds are obtained. A wide range of substrates are thus smoothly transformed to allylarenes at 50 °C in phosphate-buffered 2,2,2-trichloroethanol. The reaction concept combines the use of abundant reagents and directing groups in a sustainable, waste-minimised method for C-C bond formation.
Regiospecific ortho-C?H Allylation of Benzoic Acids
Trita, A. Stefania,Biafora, Agostino,Pichette Drapeau, Martin,Weber, Philip,Goo?en, Lukas J.
supporting information, p. 14580 - 14584 (2018/03/13)
A carboxylate-directed ortho-C?H functionalization has been developed and it allows the regiospecific introduction of allyl residues to benzoic acids. In the presence of a [Ru(p-cymene)Cl2]2 and K3PO4, benzoic acids react with allyl acetates at only 50 °C to give the corresponding ortho-allylbenzoic acids. The protocol is generally applicable to both electron-rich and electron-poor benzoic acids in combination with linear and branched allyl acetates. The products can be further functionalized in situ, for example, by double-bond migration, lactonization, or decarboxylation.
Direct carbocyclizations of benzoic acids: Catalyst-controlled synthesis of cyclic ketones and the development of tandem aHH (acyl Heck-Heck) reactions
Miles, Kelsey C.,Le, Chi,Stambuli, James P.
, p. 11336 - 11339 (2014/10/16)
The formation of exo-methylene indanones and indenones from simple ortho-allyl benzoic acid derivatives has been developed. Selective formation of the indanone or indenone products in these reactions is controlled by choice of ancillary ligand. This new process has a low environmental footprint as the products are formed in high yields using low catalyst loadings, while the only stoichiometric chemical waste generated from the reactants in the transformation is acetic acid. The conversion of the active cyclization catalyst into the Hermman-Beller palladacycle was exploited in a one-pot tandem acyl Heck-Heck (aHH) reaction, and utilized in the synthesis of donepezil. Carboxylic acids in aHH: Simple ortho-allyl benzoic acid derivatives have been utilized in an acyl Heck (aH) reaction to selectively form indanones and indenones. The conversion of the active cyclization catalyst into the Hermman-Beller palladacycle was exploited in a one-pot tandem acyl Heck-Heck (aHH) reaction to form two sp 2-sp2 bonds of (E)-trisubstituted olefins.
