Wolff Rearrangement of Oxidatively Generated α‐Oxo Gold Carbenes: An Effective Approach to Silylketenes
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 hallmark...
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| Published in | Angewandte Chemie Vol. 131; no. 16; pp. 5295 - 5299 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
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08.04.2019
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| 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.
Die Wolff‐Umlagerung wird erstmals bei der Gold‐katalysierten Oxidation von terminal TBS‐substituierten Alkinen beobachtet. Die Silylgruppe ist für diese Reaktion notwendig, und die erzeugten Silylketene sind stabil und können entweder isoliert oder auf verschiedene Weise abgefangen werden, um γ‐Lactone, α‐silylierte Carbonsäuren und Derivate oder Silylallene zu erhalten. |
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| AbstractList | 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. 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. Die Wolff‐Umlagerung wird erstmals bei der Gold‐katalysierten Oxidation von terminal TBS‐substituierten Alkinen beobachtet. Die Silylgruppe ist für diese Reaktion notwendig, und die erzeugten Silylketene sind stabil und können entweder isoliert oder auf verschiedene Weise abgefangen werden, um γ‐Lactone, α‐silylierte Carbonsäuren und Derivate oder Silylallene zu erhalten. 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. |
| Author | Zhang, Liming Zhang, Junqi Zheng, Yang Cheng, Xinpeng Xu, Xinfang |
| Author_xml | – sequence: 1 givenname: Yang surname: Zheng fullname: Zheng, Yang organization: Soochow University – sequence: 2 givenname: Junqi surname: Zhang fullname: Zhang, Junqi organization: University of California, Santa Barbara – sequence: 3 givenname: Xinpeng surname: Cheng fullname: Cheng, Xinpeng organization: University of California, Santa Barbara – sequence: 4 givenname: Xinfang surname: Xu fullname: Xu, Xinfang email: xinfangxu@suda.edu.cn organization: Soochow University – sequence: 5 givenname: Liming orcidid: 0000-0002-5306-1515 surname: Zhang fullname: Zhang, Liming email: zhang@chem.ucsb.edu organization: University of California, Santa Barbara |
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| Snippet | Gold‐catalyzed oxidations of alkynes by N‐oxides offer direct access to reactive α‐oxo gold carbene intermediates from benign and readily available alkynes... Abstract Gold‐catalyzed oxidations of alkynes by N‐oxides offer direct access to reactive α‐oxo gold carbene intermediates from benign and readily available... |
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| SubjectTerms | Alkine Alkynes Carbene Carbenes Carbonyl compounds Carbonyls Carboxylic acids Chemistry Gold Intermediates Ketene Nucleophiles Organic chemistry Oxides Umlagerungen |
| Title | Wolff Rearrangement of Oxidatively Generated α‐Oxo Gold Carbenes: An Effective Approach to Silylketenes |
| URI | https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fange.201814018 https://www.proquest.com/docview/2200870160 |
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