Alcohol-Incorporating Diels–Alder Dimerization of In Situ Formed ortho-Quinamine via Co-Nitrenoid Insertion
We disclose herein a Cp*Co(III)(LX)-catalyzed dearomative Diels–Alder dimerization of 2,6-disubstituted phenyl azidoformates. Upon the postulated cobalt-nitrenoid insertion into the neighboring ortho-carbon, the key intermediate of ortho-quinamine was generated for the subsequent dimeric cycloaddi...
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| Published in: | Organic letters Vol. 24; no. 31; pp. 5845 - 5850 |
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| Main Authors: | , , , |
| Format: | Journal Article |
| Language: | English |
| Published: |
American Chemical Society
12-08-2022
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| Online Access: | Get full text |
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| Summary: | We disclose herein a Cp*Co(III)(LX)-catalyzed dearomative Diels–Alder dimerization of 2,6-disubstituted phenyl azidoformates. Upon the postulated cobalt-nitrenoid insertion into the neighboring ortho-carbon, the key intermediate of ortho-quinamine was generated for the subsequent dimeric cycloaddition process. A series of experimental and computational studies suggested that the quinolinol ligand of the cobalt catalyst plays a crucial role in the alcoholic solvent incorporation into the o-quinamine moiety, thereby enabling the Diels–Alder dimerization to furnish the bridged tricyclic bisamidation products. |
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| Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| ISSN: | 1523-7060 1523-7052 |
| DOI: | 10.1021/acs.orglett.2c02392 |