Manganese(I)-Catalyzed C-H Aminocarbonylation of Heteroarenes
A versatile manganese(I) catalyst was employed in CH aminocarbonylation reactions of heteroarenes with aryl as well as with alkyl isocyanates using a removable directing group approach. Detailed experimental mechanistic studies were suggestive of an organometallic CH manganesation step, followed b...
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| Published in | Angewandte Chemie (International ed.) Vol. 54; no. 47; pp. 14137 - 14140 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
16.11.2015
WILEY‐VCH Verlag Wiley Wiley Subscription Services, Inc |
| Edition | International ed. in English |
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| Abstract | A versatile manganese(I) catalyst was employed in CH aminocarbonylation reactions of heteroarenes with aryl as well as with alkyl isocyanates using a removable directing group approach. Detailed experimental mechanistic studies were suggestive of an organometallic CH manganesation step, followed by a rate‐determining migratory insertion.
Heteroaromatic amides were obtained by a step‐economical, manganese(I)‐catalyzed CH aminocarbonylation reaction between heteroarenes and aryl and alkyl isocyanates. The catalytic cycle was initiated by a facile organometallic CH manganesation step, followed by a rate‐determining migratory insertion. DG = directing group. |
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| AbstractList | A versatile manganese(I) catalyst was employed in C-H aminocarbonylation reactions of heteroarenes with aryl as well as with alkyl isocyanates using a removable directing group approach. Detailed experimental mechanistic studies were suggestive of an organometallic C-H manganesation step, followed by a rate-determining migratory insertion. A versatile manganese(I) catalyst was employed in CH aminocarbonylation reactions of heteroarenes with aryl as well as with alkyl isocyanates using a removable directing group approach. Detailed experimental mechanistic studies were suggestive of an organometallic CH manganesation step, followed by a rate‐determining migratory insertion. Heteroaromatic amides were obtained by a step‐economical, manganese(I)‐catalyzed CH aminocarbonylation reaction between heteroarenes and aryl and alkyl isocyanates. The catalytic cycle was initiated by a facile organometallic CH manganesation step, followed by a rate‐determining migratory insertion. DG = directing group. Abstract A versatile manganese(I) catalyst was employed in CH aminocarbonylation reactions of heteroarenes with aryl as well as with alkyl isocyanates using a removable directing group approach. Detailed experimental mechanistic studies were suggestive of an organometallic CH manganesation step, followed by a rate‐determining migratory insertion. A versatile manganese(I) catalyst was employed in CH aminocarbonylation reactions of heteroarenes with aryl as well as with alkyl isocyanates using a removable directing group approach. Detailed experimental mechanistic studies were suggestive of an organometallic CH manganesation step, followed by a rate-determining migratory insertion. |
| Author | Bang, Jonas Liu, Weiping Zhang, Yujiao Ackermann, Lutz |
| Author_xml | – sequence: 1 givenname: Weiping surname: Liu fullname: Liu, Weiping organization: Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen (Germany) http://www.ackermann.chemie.uni-goettingen.de/ – sequence: 2 givenname: Jonas surname: Bang fullname: Bang, Jonas organization: Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen (Germany) http://www.ackermann.chemie.uni-goettingen.de/ – sequence: 3 givenname: Yujiao surname: Zhang fullname: Zhang, Yujiao organization: Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen (Germany) http://www.ackermann.chemie.uni-goettingen.de/ – sequence: 4 givenname: Lutz surname: Ackermann fullname: Ackermann, Lutz email: Lutz.Ackermann@chemie.uni-goettingen.de organization: Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen (Germany) http://www.ackermann.chemie.uni-goettingen.de/ |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/26418747$$D View this record in MEDLINE/PubMed |
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| Keywords | OXIDATION ARYLATIONS ALKYLATION reaction mechanisms AMIDATION FLUORINATION manganese FUNCTIONALIZATION indoles C-H activation isocyanates BOND ACTIVATION ARYL CYCLIZATION |
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| Snippet | A versatile manganese(I) catalyst was employed in CH aminocarbonylation reactions of heteroarenes with aryl as well as with alkyl isocyanates using a... A versatile manganese(I) catalyst was employed in C-H aminocarbonylation reactions of heteroarenes with aryl as well as with alkyl isocyanates using a... Abstract A versatile manganese(I) catalyst was employed in CH aminocarbonylation reactions of heteroarenes with aryl as well as with alkyl isocyanates using a... A versatile manganese(I) catalyst was employed in CH aminocarbonylation reactions of heteroarenes with aryl as well as with alkyl isocyanates using a removable... |
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| SubjectTerms | C-H activation Chemistry Chemistry, Multidisciplinary indoles isocyanates manganese Physical Sciences reaction mechanisms Science & Technology |
| Title | Manganese(I)-Catalyzed C-H Aminocarbonylation of Heteroarenes |
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