1322091-24-6Relevant articles and documents
Silver-Catalyzed Sequential Cascade Reaction of Isocyanides with 1-(2-Ethynyl-phenyl)-prop-2-yn-1-ol: Access to Benzo[b]fluorenes and Benzofuran-Pyrroles
Liu, Jian-Quan,Chen, Xinyi,Shen, Xuanyu,Wang, Yihan,Wang, Xiang-Shan,Bi, Xihe
supporting information, p. 1543 - 1548 (2019/02/06)
A silver-catalyzed cycloaromatization of 1-(2-ethynyl-phenyl)-prop-2-yn-1-ol with isocyanides efficiently provides benzo[b]fluorene and benzofuran-pyrrole derivatives through a modular cascade reaction that includes a nucleophilic attack on the diyne substrate. A C?C cross-coupling/oxygen transportation/Diels-Alder/hydrogen shift/isomerization cascade mechanistic pathway is proposed. (Figure presented.).
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.