ArticleAngewandte Chemie (International ed. in English)2019
Wolff Rearrangement of Oxidatively Generated α-Oxo Gold Carbenes: An Effective Approach to Silylketenes.
Article in Angewandte Chemie (International ed. in English), 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed, 52 citations in OpenAlex.
- Gold-Catalyzed Reactions between 2-Alkenyl-1-arylalkynes and Nitrones via 1,2-C,N-Difunctionalizations Together with the C═C Double Bond Cleavage.The Journal of organic chemistry · 2025Article
- Reactivities of α-Oxo BMIDA Gold Carbenes Generated by Gold-Catalyzed Oxidation of BMIDA-Terminated Alkynes.Angewandte Chemie (International ed. in English) · 2023Article
- Gold-Catalyzed Regioselective Synthesis of Crowded Cyclopentadienes by Migratory Cycloisomerization of Vinylallenes.Organic letters · 2022Article
- Homogeneous Gold-Catalyzed Oxidation Reactions.Chemical reviews · 2021Review
- Synthesis, Characterization, and Comparative Theoretical Investigation of Dinitrogen-Bridged Group 6-Gold Heterobimetallic Complexes.Inorganic chemistry · 2021Article
- Non-Diazo C-H Insertion Approach to Cyclobutanones through Oxidative Gold Catalysis.Angewandte Chemie (International ed. in English) · 2020Article
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Authors and funding
5 authors at 2 institutions in 2 countries.
Funding
Abstract
Gold-catalyzed oxidations of alkynes by N-oxides offer direct access to reactive α-oxo gold carbene intermediates from benign and readily available alkynes instead of hazardous diazo carbonyl compounds. Despite various versatile synthetic methods developed based on this strategy, one of the hallmarks of α-oxo carbene/carbenoid chemistry, that is, the Wolff rearrangement, has not been realized in this context. This study discloses the first examples that show the Wolff rearrangement can be readily realized by α-oxo gold carbenes oxidatively generated from TBS-terminated alkynes (TBS=tert-butyldimethylsilyl). The thus-generated silylketenes can be either isolated pure or subsequently trapped by various internal or external nucleophiles in one pot to afford α-silylated carboxylic acids, their derivatives, or TBS-substituted allenes.
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