4970-78-9Relevant articles and documents
Visible-Light-Induced in Situ Generation of Fischer-Type Copper Carbene Complexes from Acylsilanes and Its Application to Catalytic [4 + 1] Cycloaddition with Siloxydienes
Takeuchi, Taiichi,Aoyama, Tsukasa,Orihara, Kurumi,Ishida, Kento,Kusama, Hiroyuki
, p. 9490 - 9494 (2021/12/14)
A novel methodology for in situ generation of Fischer-type metal–carbene complexes was developed. Photoirradiation to a mixture of an acylsilane and a cationic copper complex cleanly gave a Fischer-type copper–siloxycarbene complex, which was detected by spectroscopic methods. This carbene complex reacted with siloxydienes in a [4 + 1] cycloaddition manner to give cyclopentene derivatives. It is noteworthy that this reaction proceeds with a catalytic amount of copper through in situ generation of a Fischer-type copper–siloxycarbene complex intermediate.
Regio- and stereoselective synthesis of cyclopentenones: Intermolecular Pseudo-Pauson-Khand cyclization
Barluenga, Jose,Alvarez-Fernandez, Ana,Suarez-Sobrino, Angel L.,Tomas, Miguel
supporting information; experimental part, p. 183 - 186 (2012/03/26)
Doing the two step: A very simple two-step access to polysubstituted cyclopentenones from terminal alkynes, [M(CO)6], and bromoalkenes is described. This protocol is an alternative to the intermolecular Pauson-Khand reaction, and can be used wi
Reaction of Alkynes with Cyclopropylcarbene-Chromium Complexes: A Versatile Cycloaddition Reaction for the Construction of Cyclopentenones
Tumer, Seniz U.,Herndon, James W.,McMullen, Leonard A.
, p. 8394 - 8404 (2007/10/02)
The scope and limitations of the reaction between cyclopropylcarbene-chromium complexes and alkynes have been examined.A variety of cyclopropylcarbene complexes and alkynes have been employed in these studies.The reaction appears to be general for most simple alkynes, producing cyclopentenones.A mechanism has been proposed involving metallacyclobutene formation, electrocyclic ring opening, electrocyclic ring closure, CO insertion, alkene insertion, metallacyclopentene fragmentation and cyclopentadienone reduction.The presence of these intermediates has been inferred from the structure of products obtained when the reaction was conducted in acetonitrile instead of dioxane.A trapping experiment employing 1,6-heptadiyne supports the intermediacy of vinylcarbene or vinylketene complexes.