Unlocking regioselective meta-alkylation with epoxides and oxetanes via dynamic kinetic catalyst control
Regioselective arene C−H bond alkylation is a powerful tool in synthetic chemistry, yet subject to many challenges. Herein, we report the meta -C−H bond alkylation of aromatics bearing N -directing groups using (hetero)aromatic epoxides as alkylating agents. This method results in complete regiosele...
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| Published in | Nature communications Vol. 15; no. 1; pp. 31 - 9 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
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02.01.2024
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| Abstract | Regioselective arene C−H bond alkylation is a powerful tool in synthetic chemistry, yet subject to many challenges. Herein, we report the
meta
-C−H bond alkylation of aromatics bearing
N
-directing groups using (hetero)aromatic epoxides as alkylating agents. This method results in complete regioselectivity on both the arene as well as the epoxide coupling partners, cleaving exclusively the benzylic C−O bond. Oxetanes, which are normally unreactive, also participate as alkylating reagents under the reaction conditions. Our mechanistic studies reveal an unexpected reversible epoxide ring opening process undergoing catalyst-controlled regioselection, as key for the observed high regioselectivities.
Regioselective arene C−H bond alkylation is a powerful tool in synthetic chemistry, yet subject to many challenges. Here, the authors report the meta-C−H bond alkylation of aromatics bearing N-directing groups using (hetero)aromatic epoxides as alkylating agents. |
|---|---|
| AbstractList | Regioselective arene C−H bond alkylation is a powerful tool in synthetic chemistry, yet subject to many challenges. Herein, we report the
meta
-C−H bond alkylation of aromatics bearing
N
-directing groups using (hetero)aromatic epoxides as alkylating agents. This method results in complete regioselectivity on both the arene as well as the epoxide coupling partners, cleaving exclusively the benzylic C−O bond. Oxetanes, which are normally unreactive, also participate as alkylating reagents under the reaction conditions. Our mechanistic studies reveal an unexpected reversible epoxide ring opening process undergoing catalyst-controlled regioselection, as key for the observed high regioselectivities. Abstract Regioselective arene C−H bond alkylation is a powerful tool in synthetic chemistry, yet subject to many challenges. Herein, we report the meta-C−H bond alkylation of aromatics bearing N-directing groups using (hetero)aromatic epoxides as alkylating agents. This method results in complete regioselectivity on both the arene as well as the epoxide coupling partners, cleaving exclusively the benzylic C−O bond. Oxetanes, which are normally unreactive, also participate as alkylating reagents under the reaction conditions. Our mechanistic studies reveal an unexpected reversible epoxide ring opening process undergoing catalyst-controlled regioselection, as key for the observed high regioselectivities. Regioselective arene C-H bond alkylation is a powerful tool in synthetic chemistry, yet subject to many challenges. Herein, we report the meta-C-H bond alkylation of aromatics bearing N-directing groups using (hetero)aromatic epoxides as alkylating agents. This method results in complete regioselectivity on both the arene as well as the epoxide coupling partners, cleaving exclusively the benzylic C-O bond. Oxetanes, which are normally unreactive, also participate as alkylating reagents under the reaction conditions. Our mechanistic studies reveal an unexpected reversible epoxide ring opening process undergoing catalyst-controlled regioselection, as key for the observed high regioselectivities. Regioselective arene C−H bond alkylation is a powerful tool in synthetic chemistry, yet subject to many challenges. Herein, we report the meta -C−H bond alkylation of aromatics bearing N -directing groups using (hetero)aromatic epoxides as alkylating agents. This method results in complete regioselectivity on both the arene as well as the epoxide coupling partners, cleaving exclusively the benzylic C−O bond. Oxetanes, which are normally unreactive, also participate as alkylating reagents under the reaction conditions. Our mechanistic studies reveal an unexpected reversible epoxide ring opening process undergoing catalyst-controlled regioselection, as key for the observed high regioselectivities. Regioselective arene C−H bond alkylation is a powerful tool in synthetic chemistry, yet subject to many challenges. Here, the authors report the meta-C−H bond alkylation of aromatics bearing N-directing groups using (hetero)aromatic epoxides as alkylating agents. Regioselective arene C-H bond alkylation is a powerful tool in synthetic chemistry, yet subject to many challenges. Herein, we report the meta-C-H bond alkylation of aromatics bearing N-directing groups using (hetero)aromatic epoxides as alkylating agents. This method results in complete regioselectivity on both the arene as well as the epoxide coupling partners, cleaving exclusively the benzylic C-O bond. Oxetanes, which are normally unreactive, also participate as alkylating reagents under the reaction conditions. Our mechanistic studies reveal an unexpected reversible epoxide ring opening process undergoing catalyst-controlled regioselection, as key for the observed high regioselectivities.Regioselective arene C-H bond alkylation is a powerful tool in synthetic chemistry, yet subject to many challenges. Herein, we report the meta-C-H bond alkylation of aromatics bearing N-directing groups using (hetero)aromatic epoxides as alkylating agents. This method results in complete regioselectivity on both the arene as well as the epoxide coupling partners, cleaving exclusively the benzylic C-O bond. Oxetanes, which are normally unreactive, also participate as alkylating reagents under the reaction conditions. Our mechanistic studies reveal an unexpected reversible epoxide ring opening process undergoing catalyst-controlled regioselection, as key for the observed high regioselectivities. Regioselective arene C−H bond alkylation is a powerful tool in synthetic chemistry, yet subject to many challenges. Herein, we report the meta-C−H bond alkylation of aromatics bearing N-directing groups using (hetero)aromatic epoxides as alkylating agents. This method results in complete regioselectivity on both the arene as well as the epoxide coupling partners, cleaving exclusively the benzylic C−O bond. Oxetanes, which are normally unreactive, also participate as alkylating reagents under the reaction conditions. Our mechanistic studies reveal an unexpected reversible epoxide ring opening process undergoing catalyst-controlled regioselection, as key for the observed high regioselectivities.Regioselective arene C−H bond alkylation is a powerful tool in synthetic chemistry, yet subject to many challenges. Here, the authors report the meta-C−H bond alkylation of aromatics bearing N-directing groups using (hetero)aromatic epoxides as alkylating agents. |
| ArticleNumber | 31 |
| Author | Bai, Peng-Bo Larrosa, Igor Wang, Gang-Wei Durie, Alastair |
| Author_xml | – sequence: 1 givenname: Peng-Bo surname: Bai fullname: Bai, Peng-Bo organization: State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University – sequence: 2 givenname: Alastair surname: Durie fullname: Durie, Alastair organization: School of Natural Sciences, Department of Chemistry, University of Manchester – sequence: 3 givenname: Gang-Wei orcidid: 0000-0002-3779-4495 surname: Wang fullname: Wang, Gang-Wei email: wanggw@lzu.edu.cn organization: State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University – sequence: 4 givenname: Igor orcidid: 0000-0002-5391-7424 surname: Larrosa fullname: Larrosa, Igor email: igor.larrosa@manchester.ac.uk organization: School of Natural Sciences, Department of Chemistry, University of Manchester |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/38167324$$D View this record in MEDLINE/PubMed |
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| Snippet | Regioselective arene C−H bond alkylation is a powerful tool in synthetic chemistry, yet subject to many challenges. Herein, we report the
meta
-C−H bond... Regioselective arene C-H bond alkylation is a powerful tool in synthetic chemistry, yet subject to many challenges. Herein, we report the meta-C-H bond... Regioselective arene C−H bond alkylation is a powerful tool in synthetic chemistry, yet subject to many challenges. Herein, we report the meta-C−H bond... Abstract Regioselective arene C−H bond alkylation is a powerful tool in synthetic chemistry, yet subject to many challenges. Herein, we report the meta-C−H... |
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| SubjectTerms | 140/131 140/58 639/638/403/933 639/638/403/934 639/638/77/888 Acids Alkylating agents Alkylation Aromatic compounds Catalysis Catalysts Epoxides Humanities and Social Sciences Hydrogen bonds Lead multidisciplinary Reagents Regioselectivity Ring opening Science Science (multidisciplinary) |
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| Title | Unlocking regioselective meta-alkylation with epoxides and oxetanes via dynamic kinetic catalyst control |
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