Cobalt‐Catalyzed Intramolecular Markovnikov Hydrocarbonylation of Unactivated Alkenes via Hydrogen Atom Transfer
A cobalt‐catalyzed intramolecular Markovnikov hydroalkoxycarbonylation and hydroaminocarbonylation of unactivated alkenes has been developed, enabling highly chemo‐ and regioselective synthesis of α‐alkylated γ‐lactones and α‐alkylated γ‐lactams in good yields. The mild reaction conditions allow use...
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| Published in | Angewandte Chemie Vol. 136; no. 46 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
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11.11.2024
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| Abstract | A cobalt‐catalyzed intramolecular Markovnikov hydroalkoxycarbonylation and hydroaminocarbonylation of unactivated alkenes has been developed, enabling highly chemo‐ and regioselective synthesis of α‐alkylated γ‐lactones and α‐alkylated γ‐lactams in good yields. The mild reaction conditions allow use of mono‐, di‐ and trisubstituted alkenes bearing a variety of functional groups. Preliminary mechanistic studies suggest the reaction proceeds through a CO‐mediated hydrogen atom transfer (HAT) and radical‐polar crossover (RPC) process, in which a cationic acylcobalt(IV) complex is proposed as the key intermediate.
A cobalt‐catalyzed intramolecular Markovnikov hydroalkoxycarbonylation and hydroaminocarbonylation of unactivated alkenes has been developed, enabling highly chemo‐ and regioselective synthesis of α‐alkylated γ‐lactones as well as α‐alkylated γ‐lactams under mild reaction conditions. Mechanistic studies suggest the reaction proceeds through a CO‐mediated hydrogen atom transfer (HAT) and radical‐polar crossover (RPC) process. |
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| AbstractList | A cobalt‐catalyzed intramolecular Markovnikov hydroalkoxycarbonylation and hydroaminocarbonylation of unactivated alkenes has been developed, enabling highly chemo‐ and regioselective synthesis of α‐alkylated γ‐lactones and α‐alkylated γ‐lactams in good yields. The mild reaction conditions allow use of mono‐, di‐ and trisubstituted alkenes bearing a variety of functional groups. Preliminary mechanistic studies suggest the reaction proceeds through a CO‐mediated hydrogen atom transfer (HAT) and radical‐polar crossover (RPC) process, in which a cationic acylcobalt(IV) complex is proposed as the key intermediate. A cobalt‐catalyzed intramolecular Markovnikov hydroalkoxycarbonylation and hydroaminocarbonylation of unactivated alkenes has been developed, enabling highly chemo‐ and regioselective synthesis of α‐alkylated γ‐lactones and α‐alkylated γ‐lactams in good yields. The mild reaction conditions allow use of mono‐, di‐ and trisubstituted alkenes bearing a variety of functional groups. Preliminary mechanistic studies suggest the reaction proceeds through a CO‐mediated hydrogen atom transfer (HAT) and radical‐polar crossover (RPC) process, in which a cationic acylcobalt(IV) complex is proposed as the key intermediate. A cobalt‐catalyzed intramolecular Markovnikov hydroalkoxycarbonylation and hydroaminocarbonylation of unactivated alkenes has been developed, enabling highly chemo‐ and regioselective synthesis of α‐alkylated γ‐lactones as well as α‐alkylated γ‐lactams under mild reaction conditions. Mechanistic studies suggest the reaction proceeds through a CO‐mediated hydrogen atom transfer (HAT) and radical‐polar crossover (RPC) process. |
| Author | Jiang, Donghao Li, Xinzhu Xiao, Mengdie Cheng, Li‐Jie |
| Author_xml | – sequence: 1 givenname: Donghao surname: Jiang fullname: Jiang, Donghao organization: Hunan University – sequence: 2 givenname: Xinzhu surname: Li fullname: Li, Xinzhu organization: Hunan University – sequence: 3 givenname: Mengdie surname: Xiao fullname: Xiao, Mengdie organization: Hunan University – sequence: 4 givenname: Li‐Jie orcidid: 0000-0002-3272-3276 surname: Cheng fullname: Cheng, Li‐Jie email: ljcheng@hnu.edu.cn organization: Nankai University |
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| Snippet | A cobalt‐catalyzed intramolecular Markovnikov hydroalkoxycarbonylation and hydroaminocarbonylation of unactivated alkenes has been developed, enabling highly... |
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| SubjectTerms | Alkenes Alkylation Chemical synthesis Cobalt Functional groups Hydrocarbonylation Hydrogen Atom Transfer Hydrogen atoms Lactones Markovnikov Selectivity Unactivated Alkenes |
| Title | Cobalt‐Catalyzed Intramolecular Markovnikov Hydrocarbonylation of Unactivated Alkenes via Hydrogen Atom Transfer |
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