A reagent-controlled divergent reaction of vinyl sulfoxonium ylides with arylideneindane-1,3-diones has been developed. The transformation proceeds through in situ formation and selective cleavage of donor-acceptor cyclopropane intermediates, providing dihydropyranone and indenopyranone scaffolds with excellent regio- and stereoselectivity. B(C6F5)3 affords dihydropyranones, whereas ceric ammonium nitrate (CAN) furnishes indenopyranones. Mechanistic studies identify a common vinyl cyclopropane intermediate and support distinct ionic and radical pathways.
We report a sequential one-pot gold-catalyzed cyclization/aryne cycloaddition strategy that affords structurally diverse 5-arylmethyl oxazoles and substituted polyacenes from simple propargylic amides. Arynes are shown to engage the oxazoline products from gold catalysis via an ene reaction, with the resulting oxazoles...
A. Y. R. Werling, Yun Yang, C. R. Jones· Organic Chemistry Frontiers· 0 citations
We report a phosphine-catalyzed [3 + 2] annulation of indole N-alkynamides with ynones, providing efficient access to arylidene spiro-cyclopentanone pyrroloquinolinediones. The reaction proceeds through the in situ generation of a reactive enedione intermediate and exhibits broad substrate scope, high regioselectivity,...
Raghunath Maruti Walunj, Y. Nagare, Cheng-Hao Ho et al.· Organic Letters· 0 citations
Herein, we report a one-step Pd(II)-catalyzed strategy for the synthesis of synthetically challenging and medicinally important functionalized dibenzotropone scaffolds from readily accessible o-alkynylaryl nitriles and electron-rich aryl boronic acids. The cascade process involves regioselective 1,2-syn-carbopalladatio...
Ayush Kumar, Sankar Sau, Amit Kumar· Organic Letters· 0 citations
A concise and efficient domino strategy for the synthesis of symmetrically 2,3-disubstituted indenols has been developed via palladium-catalyzed Suzuki coupling of readily accessible 1,2-diborylalkenes with substituted 2-bromoaryl carbonyl compounds. The reaction proceeds efficiently, with palladium playing a dual role...
M. Sravani, Kummari Kunta Harshitha, Jayaram Vankudoth et al.· Journal of Organic Chemistry· 0 citations
An efficient Pd-catalyzed tandem dearomative Heck reaction of N-propiolylindoles or pyrroles with aryl bromides has been developed. The protocol provides access to a series of benzopyrrolizinone and pyrrolizinone derivatives bearing a quaternary stereocenter and a tetrasubstituted olefin moiety in moderate to high yiel...
Hao Liu, Ming-Hao Yang, Ru-Xiao Li et al.· Organic Letters· 0 citations
A practical and efficient protocol for the enantioselective synthesis of seven-membered fused chromanone derivatives has been developed under mild conditions. This approach proceeds via a stepwise sequence involving a palladium-catalyzed O-allylic reaction of 3-hydroxy chromones with vinyl ethylene carbonates, followed...
Hong-Fang Xie, Zong-Li Xiong, Wei-Jun Yao et al.· Organic and biomolecular che...· 0 citations
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