Catalytic Isomerization of Unprotected Mesoionic N‐Heterocyclic Olefins and Their Lewis Adducts
Recently, novel C5‐position‐unprotected mesoionic N‐heterocyclic olefins (mNHOs) demonstrated interesting reactivity with various Lewis acids during experiments. In this work, extensive DFT calculations show that the isomerization of such mNHOs to more Lewis‐basic mesoionic carbenes (MICs) can be ef...
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| Published in | European journal of organic chemistry Vol. 2022; no. 35 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
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| Abstract | Recently, novel C5‐position‐unprotected mesoionic N‐heterocyclic olefins (mNHOs) demonstrated interesting reactivity with various Lewis acids during experiments. In this work, extensive DFT calculations show that the isomerization of such mNHOs to more Lewis‐basic mesoionic carbenes (MICs) can be efficiently catalyzed by weakly protic acidic species including C5‐unprotected mNHOs, their Lewis adducts and polar H2O molecules, thus enabling catalytic isomerization and H‐isotope exchange of such mNHOs and their Lewis adducts.
Extensive DFT calculations show that the isomerization of C5‐unprotected mesoionic N‐heterocyclic olefins (mNHOs) to more Lewis basic mesoionic carbenes (MICs) can be efficiently catalyzed by weakly protic acidic species including unprotected mNHO, MIC, their Lewis adducts and polar H2O molecules, thus enabling catalytic isomerization and H‐isotope exchange reactions of such mNHOs and their Lewis adducts. |
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| AbstractList | Recently, novel C5‐position‐unprotected mesoionic N‐heterocyclic olefins (mNHOs) demonstrated interesting reactivity with various Lewis acids during experiments. In this work, extensive DFT calculations show that the isomerization of such mNHOs to more Lewis‐basic mesoionic carbenes (MICs) can be efficiently catalyzed by weakly protic acidic species including C5‐unprotected mNHOs, their Lewis adducts and polar H2O molecules, thus enabling catalytic isomerization and H‐isotope exchange of such mNHOs and their Lewis adducts.
Extensive DFT calculations show that the isomerization of C5‐unprotected mesoionic N‐heterocyclic olefins (mNHOs) to more Lewis basic mesoionic carbenes (MICs) can be efficiently catalyzed by weakly protic acidic species including unprotected mNHO, MIC, their Lewis adducts and polar H2O molecules, thus enabling catalytic isomerization and H‐isotope exchange reactions of such mNHOs and their Lewis adducts. Recently, novel C 5 ‐position‐unprotected mesoionic N ‐heterocyclic olefins (mNHOs) demonstrated interesting reactivity with various Lewis acids during experiments. In this work, extensive DFT calculations show that the isomerization of such mNHOs to more Lewis‐basic mesoionic carbenes (MICs) can be efficiently catalyzed by weakly protic acidic species including C 5 ‐unprotected mNHOs, their Lewis adducts and polar H 2 O molecules, thus enabling catalytic isomerization and H‐isotope exchange of such mNHOs and their Lewis adducts. Recently, novel C5‐position‐unprotected mesoionic N‐heterocyclic olefins (mNHOs) demonstrated interesting reactivity with various Lewis acids during experiments. In this work, extensive DFT calculations show that the isomerization of such mNHOs to more Lewis‐basic mesoionic carbenes (MICs) can be efficiently catalyzed by weakly protic acidic species including C5‐unprotected mNHOs, their Lewis adducts and polar H2O molecules, thus enabling catalytic isomerization and H‐isotope exchange of such mNHOs and their Lewis adducts. |
| Author | Qu, Zheng‐Wang Zhu, Hui Grimme, Stefan Streubel, Rainer |
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| Snippet | Recently, novel C5‐position‐unprotected mesoionic N‐heterocyclic olefins (mNHOs) demonstrated interesting reactivity with various Lewis acids during... Recently, novel C 5 ‐position‐unprotected mesoionic N ‐heterocyclic olefins (mNHOs) demonstrated interesting reactivity with various Lewis acids during... |
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| SubjectTerms | Adducts Alkenes Density functional calculations Isomerization Lewis acid Lewis acids Mesoionic carbenes N-Heterocyclic olefins Reaction mechanism |
| Title | Catalytic Isomerization of Unprotected Mesoionic N‐Heterocyclic Olefins and Their Lewis Adducts |
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