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Cyclopenta[b]annulation of Heteroarenes by Organocatalytic γ′[C(sp3)−H] Functionalization of Ynones 下载免费PDF全文
Moluguri Raghu Dr. Jagdeep Grover Prof. Dr. S. S. V. Ramasastry 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(51):18316-18321
A new approach for the cyclopenta[b]annulation of heteroarenes through metal‐free and directing‐group‐free γ′[C(sp3)?H] functionalization and intramolecular hydroalkylation of ynones has been developed. In an unprecedented event, nucleophilic addition of an organophosphine to the designed ynones triggers γ′[C(sp3)?H] functionalization, leading to the formation of heteroaryl‐based ortho‐quinodimethane (oQDM) intermediates that undergo carbocyclization to provide cyclopentannulated heteroarenes in good yields and excellent stereoselectivities. Deuterium‐labeling experiments substantiated the proposed reaction mechanism as well as the speculated epimerization. 相似文献
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Robin Heckershoff Steffen Maier Dr. Thomas Wurm Dr. Philipp Biegger Kerstin Brödner Petra Krämer Dr. Marvin T. Hoffmann Lukas Eberle Jana Stein Dr. Frank Rominger Dr. Matthias Rudolph Dr. Jan Freudenberg Prof. Andreas Dreuw Prof. A. Stephen K. Hashmi Prof. Uwe H. F. Bunz 《Chemistry (Weinheim an der Bergstrasse, Germany)》2022,28(12):e202104203
The transition-metal-catalyzed cyclization of bissilylethynylated N,N’-dihydrotetraazapentacene (TIPS-TAP-H2) into bissilylated cyclopenta[fg,qr]pentacenes is reported. Depending on the catalyst either none, one or two silyl groups migrate and change their positions in the formed five-membered rings. The optoelectronic properties are quite similar, whereas the packing motifs differ dramatically. Control experiments and quantum chemical calculations were performed to investigate the mechanism of the reaction and the selectivity of the silyl shift. 相似文献
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Alexander Vogel Till Schreyer John Bergner Dr. Frank Rominger Dr. Thomas Oeser Prof. Dr. Milan Kivala 《Chemistry (Weinheim an der Bergstrasse, Germany)》2022,28(67):e202201424
A novel doubly cyclopentannulated carbazole which is accessible through a successive π-expansion of di(1-naphthylamine) is disclosed. The carbazole moiety is generated in the final step through intramolecular oxidative coupling. The π-expansion of carbazole resulted in strongly altered optoelectronic and electrochemical properties. The solid-state structure features an interesting packing motif with alternating face-to-face π⋅⋅⋅π and edge-to-face C−H⋅⋅⋅π interactions. The experimental findings were corroborated by theoretical calculations. 相似文献
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