107586-15-2Relevant articles and documents
Zinc-Catalyzed Tandem Diels–Alder Reactions of Enynals with Alkenes: Generation and Trapping of Cyclic o-Quinodimethanes (o-QDMs)
Zhang, Jiantao,Xiao, Yelin,Chen, Kai,Wu, Wanqing,Jiang, Huanfeng,Zhu, Shifa
, p. 2684 - 2691 (2016)
A systematic investigation of ZnCl2-catalyzed reactions of enynals with alkenes has been undertaken. Structurally unique propeller-like products could be obtained under mild conditions. Cyclic o-quinodimethanes (o-QDMs) are generated through [4+2] cycloaddition between enynals and alkenes. Both electron-poor and electron-rich dienophiles could be used to trap the active intermediate through [4+2] cycloaddition. But [1,5]-H shift products could also be observed when electron-rich alkenes were used as dienophile. DFT calculations were performed to understand the reaction mechanism. A competition between the [4+2] cycloaddition and [1,5]-H shift was proposed for the transformation of cyclic o-QDMs. The selectivity could be affected by the properties of the substrates. (Figure presented.).
Gold Catalysis Meets Materials Science – A New Approach to π-Extended Indolocarbazoles
Hendrich, Christoph M.,Bongartz, Lukas M.,Hoffmann, Marvin T.,Zschieschang, Ute,Borchert, James W.,Sauter, Désirée,Kr?mer, Petra,Rominger, Frank,Mulks, Florian F.,Rudolph, Matthias,Dreuw, Andreas,Klauk, Hagen,Hashmi, A. Stephen K.
supporting information, p. 549 - 557 (2020/12/07)
Herein we describe a modular, convergent synthesis of substituted benzo[a]benzo[6,7]-indolo[2,3-h]carbazoles (BBICZs) using a bidirectional gold-catalyzed cyclization reaction as a key step. A building block strategy enabled the easy variation of substituents at different positions of the core structure and a general analysis of substitution effects on the materials properties of the target compounds. All BBICZs were fully characterized and their optical and electronic properties were studied experimentally as well as by computational methods. Organic thin-film transistors based on eight selected derivatives were fabricated by vacuum deposition and charge-carrier mobilities up to 1 cm2/Vs were measured. (Figure presented.).
Gold-Catalyzed Cyclization of 2-Alkynylaldehyde Cyclic Acetals via Hydride Shift for the Synthesis of Indenone Derivatives
Yamada, Tsuyoshi,Park, Kwihwan,Tachikawa, Takumu,Fujii, Akiko,Rudolph, Matthias,Hashmi, A. Stephen K.,Sajiki, Hironao
supporting information, p. 1883 - 1888 (2020/03/03)
An efficient gold-catalyzed cyclization of 2-alkynylaldehyde cyclic acetals has been developed for the synthesis of indenone derivatives. A wide variety of functionalized indenone derivatives can be obtained in good-to-excellent yields. HMBC and NOESY NMR analyses and mechanistic elucidation experiments revealed that the cyclization occurs via a 1,5-H shift. The cyclic acetal group promoted the 1,5-H shift by activating the benzylic C-H bond and preventing the migration of the alkoxy group by tethering both alkoxy groups.
Gold-Catalyzed Ring Expansion of Enyne-Lactone: Generation and Transformation of 2-Oxoninonium
Luo, Kui,Cao, Tongxiang,Jiang, Huanfeng,Chen, Lianfen,Zhu, Shifa
supporting information, p. 5856 - 5859 (2017/11/10)
An efficient gold-catalyzed ring-expansion reaction of enyne-lactones to form 2-oxoninonium intermediates is reported. The 2-oxoninonium generated in this work could undergo further 6π electrocyclization and aromatization reaction to produce different aromatic compounds.