Cp-Free Cobalt-Catalyzed C–H Activation/Annulations by Traceless N,O‑Bidentate Directing Group: Access to Isoquinolines
N,O-Bidentate directing-enabled, traceless heterocycle synthesis is described via Cp*-free cobalt-catalyzed C–H activation/annulation. The weakly coordinating nature of the carboxylic acid was employed for the preparation of isoquinolines. Meanwhile, the N–O bond of the α-imino-oxy acid can serve as...
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| Published in | Organic letters Vol. 21; no. 8; pp. 2863 - 2866 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
19.04.2019
Amer Chemical Soc |
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| Abstract | N,O-Bidentate directing-enabled, traceless heterocycle synthesis is described via Cp*-free cobalt-catalyzed C–H activation/annulation. The weakly coordinating nature of the carboxylic acid was employed for the preparation of isoquinolines. Meanwhile, the N–O bond of the α-imino-oxy acid can serve as an internal oxidant. Terminal as well as internal alkynes can be efficiently applied to the catalytic system. This operationally simple approach shows a broad substrate scope with the products obtained in good to excellent yields. |
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| AbstractList | N, O-Bidentate directing-enabled, traceless heterocycle synthesis is described via Cp*-free cobalt-catalyzed C-H activation/annulation. The weakly coordinating nature of the carboxylic acid was employed for the preparation of isoquinolines. Meanwhile, the N-O bond of the α-imino-oxy acid can serve as an internal oxidant. Terminal as well as internal alkynes can be efficiently applied to the catalytic system. This operationally simple approach shows a broad substrate scope with the products obtained in good to excellent yields.N, O-Bidentate directing-enabled, traceless heterocycle synthesis is described via Cp*-free cobalt-catalyzed C-H activation/annulation. The weakly coordinating nature of the carboxylic acid was employed for the preparation of isoquinolines. Meanwhile, the N-O bond of the α-imino-oxy acid can serve as an internal oxidant. Terminal as well as internal alkynes can be efficiently applied to the catalytic system. This operationally simple approach shows a broad substrate scope with the products obtained in good to excellent yields. N,O-Bidentate directing-enabled, traceless heterocycle synthesis is described via Cp*-free cobalt-catalyzed C-H activation/annulation. The weakly coordinating nature of the carboxylic acid was employed for the preparation of isoquinolines. Meanwhile, the N-O bond of the alpha-imino-oxy acid can serve as an internal oxidant. Terminal as well as internal alkynes can be efficiently applied to the catalytic system. This operationally simple approach shows a broad substrate scope with the products obtained in good to excellent yields. N,O-Bidentate directing-enabled, traceless heterocycle synthesis is described via Cp*-free cobalt-catalyzed C–H activation/annulation. The weakly coordinating nature of the carboxylic acid was employed for the preparation of isoquinolines. Meanwhile, the N–O bond of the α-imino-oxy acid can serve as an internal oxidant. Terminal as well as internal alkynes can be efficiently applied to the catalytic system. This operationally simple approach shows a broad substrate scope with the products obtained in good to excellent yields. |
| Author | Song, Mao-Ping Li, Xiao-Cai Du, Cong Niu, Jun-Long Zhang, He |
| AuthorAffiliation | College of Chemistry and Molecular Engineering |
| AuthorAffiliation_xml | – name: College of Chemistry and Molecular Engineering |
| Author_xml | – sequence: 1 givenname: Xiao-Cai surname: Li fullname: Li, Xiao-Cai – sequence: 2 givenname: Cong surname: Du fullname: Du, Cong – sequence: 3 givenname: He surname: Zhang fullname: Zhang, He – sequence: 4 givenname: Jun-Long orcidid: 0000-0001-8012-4676 surname: Niu fullname: Niu, Jun-Long email: niujunlong@zzu.edu.cn – sequence: 5 givenname: Mao-Ping orcidid: 0000-0003-3883-2622 surname: Song fullname: Song, Mao-Ping email: mpsong@zzu.edu.cn |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/30925059$$D View this record in MEDLINE/PubMed |
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| Keywords | FUNCTIONALIZATION MILD SUBSTITUTED ISOQUINOLINES 4+2 ANNULATION O BOND IMINES BOND FORMATION C(SP)-H ALKYNES |
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| Snippet | N,O-Bidentate directing-enabled, traceless heterocycle synthesis is described via Cp*-free cobalt-catalyzed C–H activation/annulation. The weakly coordinating... N,O-Bidentate directing-enabled, traceless heterocycle synthesis is described via Cp*-free cobalt-catalyzed C-H activation/annulation. The weakly coordinating... N, O-Bidentate directing-enabled, traceless heterocycle synthesis is described via Cp*-free cobalt-catalyzed C-H activation/annulation. The weakly coordinating... |
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| SubjectTerms | alkynes carbon-hydrogen bond activation carboxylic acids chemical bonding chemical reactions chemical structure Chemistry Chemistry, Organic isoquinolines oxidants Physical Sciences Science & Technology |
| Title | Cp-Free Cobalt-Catalyzed C–H Activation/Annulations by Traceless N,O‑Bidentate Directing Group: Access to Isoquinolines |
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