Construction of Quaternary Carbon Center via NHC Catalysis Initiated by an Intermolecular Heck-Type Alkyl Radical Addition

A quaternary carbon center containing an oxindole motif is constructed via NHC-catalyzed transition-metal and aldehyde-free intermolecular Heck-type alkyl radical addition initiated annulation. This redox-neutral protocol also features a simple procedure, broad substrate scope, good functional group...

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Published inOrganic letters Vol. 23; no. 12; pp. 4662 - 4666
Main Authors Su, Lanjun, Sun, Huan, Liu, Jikai, Wang, Chengming
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.06.2021
Amer Chemical Soc
Subjects
carbon
catalytic activity
cations
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
REACTIVITY
OXINDOLES
BUTOXIDE
HETEROCYCLES
C-H
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Abstract A quaternary carbon center containing an oxindole motif is constructed via NHC-catalyzed transition-metal and aldehyde-free intermolecular Heck-type alkyl radical addition initiated annulation. This redox-neutral protocol also features a simple procedure, broad substrate scope, good functional group tolerance and could be smoothly amplified to a gram scale. The mechanism study shows that the reaction possibly undergoes two folds of SET processes with an NHC radical cation intermediate involved.
AbstractList A quaternary carbon center containing an oxindole motif is constructed via NHC-catalyzed transition-metal and aldehyde-free intermolecular Heck-type alkyl radical addition initiated annulation. This redox-neutral protocol also features a simple procedure, broad substrate scope, good functional group tolerance and could be smoothly amplified to a gram scale. The mechanism study shows that the reaction possibly undergoes two folds of SET processes with an NHC radical cation intermediate involved.
A quaternary carbon center containing an oxindole motif is constructed via NHC-catalyzed transition-metal and aldehyde-free intermolecular Heck-type alkyl radical addition initiated annulation. This redox-neutral protocol also features a simple procedure, broad substrate scope, good functional group tolerance and could be smoothly amplified to a gram scale. The mechanism study shows that the reaction possibly undergoes two folds of SET processes with an NHC radical cation intermediate involved.A quaternary carbon center containing an oxindole motif is constructed via NHC-catalyzed transition-metal and aldehyde-free intermolecular Heck-type alkyl radical addition initiated annulation. This redox-neutral protocol also features a simple procedure, broad substrate scope, good functional group tolerance and could be smoothly amplified to a gram scale. The mechanism study shows that the reaction possibly undergoes two folds of SET processes with an NHC radical cation intermediate involved.
Author Liu, Jikai
Sun, Huan
Su, Lanjun
Wang, Chengming
AuthorAffiliation Department of Chemistry, College of Chemistry and Materials Science
School of Pharmaceutical Sciences
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  surname: Liu
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  surname: Wang
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  email: cmwang2019@jnu.edu.cn
  organization: Department of Chemistry, College of Chemistry and Materials Science
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Keywords REACTIVITY
OXINDOLES
BUTOXIDE
HETEROCYCLES
C-H
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Snippet A quaternary carbon center containing an oxindole motif is constructed via NHC-catalyzed transition-metal and aldehyde-free intermolecular Heck-type alkyl...
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SubjectTerms carbon
catalytic activity
cations
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Title Construction of Quaternary Carbon Center via NHC Catalysis Initiated by an Intermolecular Heck-Type Alkyl Radical Addition
URI http://dx.doi.org/10.1021/acs.orglett.1c01400
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