1314247-93-2Relevant academic research and scientific papers
Intramolecular anti-Phosphinoauration of Alkynes: An FLP-Motivated Approach to Stable Aurated Phosphindolium Complexes
Arndt, Sebastian,Hansmann, Max M.,Motloch, Petr,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
supporting information, p. 2542 - 2547 (2017/03/06)
The synthesis of aurated phosphindolium complexes from easy accessible 1,5-alkynylphosphine derivatives has been studied by using gold(I) complexes featuring carbene and phosphine ligands as initiators. Upon formation of the mixed phosphine NHC/phosphine
Insights into the Gold-Catalyzed Propargyl Ester Rearrangement/Tandem Cyclization Sequence: Radical versus Gold Catalysis - Myers-Saito- versus Schmittel-Type Cyclization
Rettenmeier, Eva,Hansmann, Max M.,Ahrens, Alexander,Rübenacker, Katharina,Saboo, Tapish,Massholder, Joy,Meier, Christian,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
supporting information, p. 14401 - 14409 (2015/10/05)
A detailed study of the gold-catalyzed tandem 1,3-carboxy migration/allene-enyne cycloisomerization was undertaken. It was found that after the initial allene formation the selectivity of the reaction is strongly influenced by the polarization of the remaining alkyne. Depending on the substitution pattern of the starting diynes, either a Schmittel- or a Myers-Saito-type cyclization was triggered. The 6-endo-dig Myers-Saito-type cyclization gave access to benzo[b]fluorenes, while the Schmittel pathway (5-exo-dig) delivered benzofulvenes as final products. In special cases a yet unknown pathway was opened by the ambiphilic nature of the allene moiety. In these cases completely different products were obtained by the nucleophilic attack of the alkyne moiety onto the allene that can also act as an electrophile. Mechanistic studies revealed that diradical pathways can be ruled out for this type of tandem cyclization reactions and it is shown that both steps of the reaction cascade are catalyzed by the gold complex.
Gold(III)- versus gold(I)-induced cyclization: Synthesis of six-membered mesoionic carbene and acyclic (aryl)(heteroaryl) carbene complexes
Ung, Ga?l,Soleilhavoup, Michele,Bertrand, Guy
supporting information, p. 758 - 761 (2013/02/23)
The golden state: Selective 5-exo- and 6-endo-cyclizations of an alkynyl benzothioamide have been achieved. The selectivity is controlled by the oxidation state of the gold precursor (+I or +III), yielding two new types of carbene ligand: an (aryl)(heteroaryl)carbene and a six-membered mesoionic carbene (see scheme). Mes=2,4,6-trimethylphenyl. Copyright
