131035-48-8Relevant academic research and scientific papers
Oxidant speciation and anionic ligand effects in the gold-catalyzed oxidative coupling of arenes and alkynes
Hofer, Manuel,De Haro, Teresa,Gómez-Bengoa, Enrique,Genoux, Alexandre,Nevado, Cristina
, p. 8411 - 8420 (2019/09/30)
The mechanism of the gold-catalyzed oxidative cross-coupling of arenes and alkynes has been studied in detail combining stoichiometric experiments with putative reaction intermediates and DFT calculations. Our data suggest that ligand exchange between the alkyne, the Au(i)-catalyst and the hypervalent iodine reagent is responsible for the formation of both an Au(i)-acetylide complex and a more reactive "non-symmetric" I(iii) oxidant responsible for the crucial Au(i)/Au(iii) turnover. Further, the reactivity of the in situ generated Au(iii)-acetylide complex is governed by the nature of the anionic ligands transferred by the I(iii) oxidant: while halogen ligands remain unreactive, acetato ligands are efficiently displaced by the arene to yield the observed Csp2-Csp cross-coupling products through an irreversible reductive elimination step. Finally, the nature of competitive processes and catalyst deactivation pathways has also been unraveled. This detailed investigation provides insights not only on the specific features of the species involved in oxidative gold-catalyzed cross couplings but also highlights the importance of both ancillary and anionic ligands in the reactivity of the key Au(iii) intermediates.
Gold-catalyzed ethynylation of arenes
De Haro, Teresa,Nevado, Cristina
supporting information; experimental part, p. 1512 - 1513 (2010/04/04)
(Figure Presented) A novel gold-catalyzed ethynylation of aromatic rings with electron-deficient alkynes via gold catalyzed C-H activation of both C sp-H and Csp2-H bonds has been developed. This transformation provides aromatic propiolates difficult to prepare by other methods, highlighting the synthetic potential of gold chemistry.
Synthesis based on Cyclohexadienes: Part 4. Novel Synthesis of the 6-Aryl-2,4-dimethoxybenzoates. Alternariol and Methyl Trimethylaltenusin
Kanakam, Charles C.,Mani, N. S.,Rao, G. S. R. Subba
, p. 2233 - 2237 (2007/10/02)
A novel method for the preparation of 6-aryl-2,4-dimethoxybenzoic acids involving the Alder-Rickert reaction of 1,5-dimethoxycyclohexa-1,4-dienes and arylpropiolic esters is described.This strategy has been extended to the synthesis of the mould metabolite alternariol and methyl trimethylaltenusin.
