Visible Light-Promoted Photocatalytic C‑5 Carboxylation of 8‑Aminoquinoline Amides and Sulfonamides via a Single Electron Transfer Pathway

An efficient photocatalytic method was developed for the remote C5-H bond carboxylation of 8-aminoquinoline amide and sulfonamide derivatives. This methodology uses in situ generated •CBr3 radical as a carboxylation agent with alcohol and is further extended to a variety of arenes and heteroarenes t...

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Published inJournal of organic chemistry Vol. 84; no. 16; pp. 9869 - 9896
Main Authors Sen, Chiranjit, Sahoo, Tapan, Singh, Harshvardhan, Suresh, Eringathodi, Ghosh, Subhash Chandra
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.08.2019
Amer Chemical Soc
Subjects
alcohols
aminoquinolines
aromatic hydrocarbons
carboxylation
cations
chemical structure
Chemistry
Chemistry, Organic
electron transfer
mass spectrometry
organic chemistry
photocatalysis
Physical Sciences
Science & Technology
sulfonamides
QUINOLINE N-OXIDES
POSITION
REGIOSELECTIVE C
ALKYLATION
ARYLATION
MERGING PHOTOREDOX CATALYSIS
INHIBITORS
C-H FUNCTIONALIZATION
METAL-FREE
C5-H PHOSPHONATION
Online AccessGet full text
ISSN0022-3263
1520-6904
1520-6904
DOI10.1021/acs.joc.9b00942

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Abstract An efficient photocatalytic method was developed for the remote C5-H bond carboxylation of 8-aminoquinoline amide and sulfonamide derivatives. This methodology uses in situ generated •CBr3 radical as a carboxylation agent with alcohol and is further extended to a variety of arenes and heteroarenes to synthesize the desired carboxylated product in moderate-to-good yields. The reaction proceeding through a single electron transfer pathway was established by a control experiment, and a butylated hydroxytoluene-trapped aryl radical cation intermediate in high-resolution mass spectrometry was identified.
AbstractList An efficient photocatalytic method was developed for the remote C5-H bond carboxylation of 8-aminoquinoline amide and sulfonamide derivatives. This methodology uses in situ generated •CBr₃ radical as a carboxylation agent with alcohol and is further extended to a variety of arenes and heteroarenes to synthesize the desired carboxylated product in moderate-to-good yields. The reaction proceeding through a single electron transfer pathway was established by a control experiment, and a butylated hydroxytoluene-trapped aryl radical cation intermediate in high-resolution mass spectrometry was identified.
An efficient photocatalytic method was developed for the remote C5-H bond carboxylation of 8-aminoquinoline amide and sulfonamide derivatives. This methodology uses in situ generated CBr radical as a carboxylation agent with alcohol and is further extended to a variety of arenes and heteroarenes to synthesize the desired carboxylated product in moderate-to-good yields. The reaction proceeding through a single electron transfer pathway was established by a control experiment, and a butylated hydroxytoluene-trapped aryl radical cation intermediate in high-resolution mass spectrometry was identified.
An efficient photocatalytic method was developed for the remote C5-H bond carboxylation of 8-aminoquinoline amide and sulfonamide derivatives. This methodology uses in situ generated (CBr3)-C-center dot radical as a carboxylation agent with alcohol and is further extended to a variety of arenes and heteroarenes to synthesize the desired carboxylated product in moderate-to-good yields. The reaction proceeding through a single electron transfer pathway was established by a control experiment, and a butylated hydroxytoluene-trapped aryl radical cation intermediate in high-resolution mass spectrometry was identified.
An efficient photocatalytic method was developed for the remote C5-H bond carboxylation of 8-aminoquinoline amide and sulfonamide derivatives. This methodology uses in situ generated •CBr3 radical as a carboxylation agent with alcohol and is further extended to a variety of arenes and heteroarenes to synthesize the desired carboxylated product in moderate-to-good yields. The reaction proceeding through a single electron transfer pathway was established by a control experiment, and a butylated hydroxytoluene-trapped aryl radical cation intermediate in high-resolution mass spectrometry was identified.
An efficient photocatalytic method was developed for the remote C5-H bond carboxylation of 8-aminoquinoline amide and sulfonamide derivatives. This methodology uses in situ generated •CBr3 radical as a carboxylation agent with alcohol and is further extended to a variety of arenes and heteroarenes to synthesize the desired carboxylated product in moderate-to-good yields. The reaction proceeding through a single electron transfer pathway was established by a control experiment, and a butylated hydroxytoluene-trapped aryl radical cation intermediate in high-resolution mass spectrometry was identified.An efficient photocatalytic method was developed for the remote C5-H bond carboxylation of 8-aminoquinoline amide and sulfonamide derivatives. This methodology uses in situ generated •CBr3 radical as a carboxylation agent with alcohol and is further extended to a variety of arenes and heteroarenes to synthesize the desired carboxylated product in moderate-to-good yields. The reaction proceeding through a single electron transfer pathway was established by a control experiment, and a butylated hydroxytoluene-trapped aryl radical cation intermediate in high-resolution mass spectrometry was identified.
Author Suresh, Eringathodi
Sen, Chiranjit
Ghosh, Subhash Chandra
Sahoo, Tapan
Singh, Harshvardhan
AuthorAffiliation Analytical and Environmental Science Division and Centralized Instrument Facility
Central Salt and Marine Chemicals Research Institute (CSIR-CSMCRI)
Academy of Scientific and Innovative Research (AcSIR)
Natural Products and Green Chemistry Division
AuthorAffiliation_xml – name: Central Salt and Marine Chemicals Research Institute (CSIR-CSMCRI)
– name: Academy of Scientific and Innovative Research (AcSIR)
– name: Analytical and Environmental Science Division and Centralized Instrument Facility
– name: Natural Products and Green Chemistry Division
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  orcidid: 0000-0002-1934-6832
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  orcidid: 0000-0002-6528-1582
  surname: Ghosh
  fullname: Ghosh, Subhash Chandra
  email: scghosh@csmcri.res.in
BackLink https://www.ncbi.nlm.nih.gov/pubmed/31307188$$D View this record in MEDLINE/PubMed
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Issue 16
Keywords QUINOLINE N-OXIDES
POSITION
REGIOSELECTIVE C
ALKYLATION
ARYLATION
MERGING PHOTOREDOX CATALYSIS
INHIBITORS
C-H FUNCTIONALIZATION
METAL-FREE
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Snippet An efficient photocatalytic method was developed for the remote C5-H bond carboxylation of 8-aminoquinoline amide and sulfonamide derivatives. This methodology...
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SubjectTerms alcohols
aminoquinolines
aromatic hydrocarbons
carboxylation
cations
chemical structure
Chemistry
Chemistry, Organic
electron transfer
mass spectrometry
organic chemistry
photocatalysis
Physical Sciences
Science & Technology
sulfonamides
Title Visible Light-Promoted Photocatalytic C‑5 Carboxylation of 8‑Aminoquinoline Amides and Sulfonamides via a Single Electron Transfer Pathway
URI http://dx.doi.org/10.1021/acs.joc.9b00942
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https://www.ncbi.nlm.nih.gov/pubmed/31307188
https://www.proquest.com/docview/2258751452
https://www.proquest.com/docview/2305178889
Volume 84
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