1566-67-2Relevant articles and documents
Stereoselective synthesis of enol acetates by the reaction of alkenylboronates with (diacetoxyiodo)benzene and sodium iodide
Murata, Miki,Satoh, Kaname,Watanabe, Shinji,Masuda, Yuzuru
, p. 1465 - 1466 (1998)
Stereochemically pure (E)- and (Z)-alk-1-en-1-yl acetates have been easily prepared by acetoxylation of the (Z)-and (E)-alk-1-en-1-ylboronic acids or their esters, respectively, with (diacetoxyiodo)benzene and sodium iodide, in reasonable yields.
Carboxylic acid addition to terminal alkynes utilizing ammonium tagged Hoveyda-Grubbs catalyst supported on magnetically separable core/shell silica: A highly reusable and air compatible catalytic system
?ztürk, Bengi ?zgün,Gürcü, Didar,?ehito?lu, Solmaz Karabulut
, p. 11 - 16 (2019/01/24)
In this study, the performance of ammonium tagged Hoveyda-Grubbs catalyst supported on magnetically separable core/shell silica gel was tested on carboxylic acid addition reactions to terminal alkynes using a variety of carboxylic acid derivatives under air atmosphere. The catalytic system was found to be compatible with air atmosphere and can tolerate even non-degassed solvents. The reaction parameters such as temperature, substrate/catalyst ratio and the effect of carboxylic acid on the selectivity and yield of the reaction were investigated in details. The reaction of arylacetylenes with acetic acid yielded the corresponding E-isomer with conversion values up to 99% with a catalytic loading of 1% Ru. The reusability of the catalyst was tested using acetic acid/benzoic acid and phenylacetylene in toluene at 85 °C under air atmosphere. The catalyst was found to be highly reusable and maintained its activity up to 11th run, reaching a conversion value of 83% with minimum ruthenium leaching.
Iron-Catalyzed Cross-Coupling of Alkenyl Acetates
G?rtner, Dominik,Stein, André Luiz,Grupe, Sabine,Arp, Johannes,Von Wangelin, Axel Jacobi
supporting information, p. 10545 - 10549 (2015/09/02)
Stable C-O linkages are generally unreactive in cross-coupling reactions which mostly employ more electrophilic halides or activated esters (triflates, tosylates). Acetates are cheap and easily accessible electrophiles but have not been used in cross-couplings because the strong C-O bond and high propensity to engage in unwanted acetylation and deprotonation. Reported herein is a selective iron-catalyzed cross-coupling of diverse alkenyl acetates, and it operates under mild reaction conditions (0 C, 2 h) with a ligand-free catalyst (1-2 mol%). Iron clad: Acetates are underutilized electrophiles in metal-catalyzed cross-coupling reactions because of the strong alkenyl C-O bond and their propensity to engage in unwanted reactions. Combination of a ligand-free low-valent Fe catalyst with nucleophilic organomagnesium reagents, low temperature, and short reaction times results in highly selective cross-couplings with alkenyl acetates.
