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 inAngewandte Chemie International Edition Vol. 63; no. 46; pp. e202412828 - n/a
Main Authors Jiang, Donghao, Li, Xinzhu, Xiao, Mengdie, Cheng, Li‐Jie
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 11.11.2024
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Alkenes
Alkylation
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Cobalt
Functional groups
Hydrocarbonylation
Hydrogen Atom Transfer
Hydrogen atoms
Lactones
Markovnikov Selectivity
Physical Sciences
Science & Technology
Unactivated Alkenes
Unactivated Alkenes
CYCLOCARBONYLATION
HYDROFUNCTIONALIZATION
Hydrogen Atom Transfer
HYDROAMINATION
Cobalt
HYDROAMINOCARBONYLATION
Hydrocarbonylation
ALLYLIC ALCOHOLS
AMINES
HYDROALKOXYLATION
Markovnikov Selectivity
OLEFINS
HYDROHYDRAZINATION
HYDROFORMYLATION
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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.
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 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.
A cobalt-catalyzed intramolecular Markovnikov hydroalkoxycarbonylation and hydroaminocarbonylation of unactivated alkenes has been developed, enabling highly chemo- and regioselective synthesis of alpha-alkylated gamma-lactones and alpha-alkylated gamma-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 alpha-alkylated gamma-lactones as well as alpha-alkylated gamma-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. image
Author Jiang, Donghao
Li, Xinzhu
Xiao, Mengdie
Cheng, Li‐Jie
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  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
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  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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crossref_primary_10_1007_s11426_024_2535_y
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Issue 46
Keywords Unactivated Alkenes
CYCLOCARBONYLATION
HYDROFUNCTIONALIZATION
Hydrogen Atom Transfer
HYDROAMINATION
Cobalt
HYDROAMINOCARBONYLATION
Hydrocarbonylation
ALLYLIC ALCOHOLS
AMINES
HYDROALKOXYLATION
Markovnikov Selectivity
OLEFINS
HYDROHYDRAZINATION
HYDROFORMYLATION
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Snippet A cobalt‐catalyzed intramolecular Markovnikov hydroalkoxycarbonylation and hydroaminocarbonylation of unactivated alkenes has been developed, enabling highly...
A cobalt-catalyzed intramolecular Markovnikov hydroalkoxycarbonylation and hydroaminocarbonylation of unactivated alkenes has been developed, enabling highly...
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StartPage e202412828
SubjectTerms Alkenes
Alkylation
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Cobalt
Functional groups
Hydrocarbonylation
Hydrogen Atom Transfer
Hydrogen atoms
Lactones
Markovnikov Selectivity
Physical Sciences
Science & Technology
Unactivated Alkenes
Title Cobalt‐Catalyzed Intramolecular Markovnikov Hydrocarbonylation of Unactivated Alkenes via Hydrogen Atom Transfer
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.202412828
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https://www.ncbi.nlm.nih.gov/pubmed/39103315
https://www.proquest.com/docview/3123670474
https://www.proquest.com/docview/3089505055
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