Direct One-Pot Synthesis of Primary 4-Amino-2,3-diaryl-quinolines via Suzuki-Miyaura Cross-Coupling of 2-Aryl-4-azido-3-iodoquinolines with Arylboronic Acids

Direct One-Pot Synthesis of Primary 4-Amino-2,3-diaryl-quinolines via Suzuki-Miyaura Cross-Coupling of 2-Aryl-4-azido-3-iodoquinolines with Arylboronic Acids

Palladium-catalyzed Suzuki-Miyaura cross-coupling of 2-aryl-4-azido-3-iodo-quinolines with arylboronic acids afforded the corresponding primary 4-amino-2,3-diarylquinolines in a single-pot operation along with symmetrical biaryls and traces of the 2,3-diaryl-4-azidoquinolines. A plausible mechanism,...

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Bibliographic Details
Main Authors: Mamasegare Mabel Mphahlele, Malose Jack Mphahlele
Format: Article
Language:English
Published: MDPI AG 2011-10-01
Series:Molecules
Subjects:
2-aryl-4-azido-3-iodoquinolines
Suzuki-Miyaura cross-coupling
symmetrical biaryls
4-azido-2,3-diarylquinolines
4-amino-2,3-diarylquinolines
Online Access:http://www.mdpi.com/1420-3049/16/11/8958/
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spelling doaj-6e575ea1492949799accdd8ff77d34642020-11-24T23:35:43ZengMDPI AGMolecules1420-30492011-10-0116118958897210.3390/molecules16118958Direct One-Pot Synthesis of Primary 4-Amino-2,3-diaryl-quinolines via Suzuki-Miyaura Cross-Coupling of 2-Aryl-4-azido-3-iodoquinolines with Arylboronic AcidsMamasegare Mabel MphahleleMalose Jack MphahlelePalladium-catalyzed Suzuki-Miyaura cross-coupling of 2-aryl-4-azido-3-iodo-quinolines with arylboronic acids afforded the corresponding primary 4-amino-2,3-diarylquinolines in a single-pot operation along with symmetrical biaryls and traces of the 2,3-diaryl-4-azidoquinolines. A plausible mechanism, which implicates palladium hydride species in the reduction of the incipient 2,3-diaryl-4-azidoquinolines to afford the 4-amino-2,3-diarylquinolines is proposed.http://www.mdpi.com/1420-3049/16/11/8958/2-aryl-4-azido-3-iodoquinolinesSuzuki-Miyaura cross-couplingsymmetrical biaryls4-azido-2,3-diarylquinolines4-amino-2,3-diarylquinolines
collection DOAJ
language English
format Article
sources DOAJ
author Mamasegare Mabel Mphahlele
Malose Jack Mphahlele
spellingShingle Mamasegare Mabel Mphahlele
Malose Jack Mphahlele
Direct One-Pot Synthesis of Primary 4-Amino-2,3-diaryl-quinolines via Suzuki-Miyaura Cross-Coupling of 2-Aryl-4-azido-3-iodoquinolines with Arylboronic Acids
Molecules
2-aryl-4-azido-3-iodoquinolines
Suzuki-Miyaura cross-coupling
symmetrical biaryls
4-azido-2,3-diarylquinolines
4-amino-2,3-diarylquinolines
author_facet Mamasegare Mabel Mphahlele
Malose Jack Mphahlele
author_sort Mamasegare Mabel Mphahlele
title Direct One-Pot Synthesis of Primary 4-Amino-2,3-diaryl-quinolines via Suzuki-Miyaura Cross-Coupling of 2-Aryl-4-azido-3-iodoquinolines with Arylboronic Acids
title_short Direct One-Pot Synthesis of Primary 4-Amino-2,3-diaryl-quinolines via Suzuki-Miyaura Cross-Coupling of 2-Aryl-4-azido-3-iodoquinolines with Arylboronic Acids
title_full Direct One-Pot Synthesis of Primary 4-Amino-2,3-diaryl-quinolines via Suzuki-Miyaura Cross-Coupling of 2-Aryl-4-azido-3-iodoquinolines with Arylboronic Acids
title_fullStr Direct One-Pot Synthesis of Primary 4-Amino-2,3-diaryl-quinolines via Suzuki-Miyaura Cross-Coupling of 2-Aryl-4-azido-3-iodoquinolines with Arylboronic Acids
title_full_unstemmed Direct One-Pot Synthesis of Primary 4-Amino-2,3-diaryl-quinolines via Suzuki-Miyaura Cross-Coupling of 2-Aryl-4-azido-3-iodoquinolines with Arylboronic Acids
title_sort direct one-pot synthesis of primary 4-amino-2,3-diaryl-quinolines via suzuki-miyaura cross-coupling of 2-aryl-4-azido-3-iodoquinolines with arylboronic acids
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2011-10-01
description Palladium-catalyzed Suzuki-Miyaura cross-coupling of 2-aryl-4-azido-3-iodo-quinolines with arylboronic acids afforded the corresponding primary 4-amino-2,3-diarylquinolines in a single-pot operation along with symmetrical biaryls and traces of the 2,3-diaryl-4-azidoquinolines. A plausible mechanism, which implicates palladium hydride species in the reduction of the incipient 2,3-diaryl-4-azidoquinolines to afford the 4-amino-2,3-diarylquinolines is proposed.
topic 2-aryl-4-azido-3-iodoquinolines
Suzuki-Miyaura cross-coupling
symmetrical biaryls
4-azido-2,3-diarylquinolines
4-amino-2,3-diarylquinolines
url http://www.mdpi.com/1420-3049/16/11/8958/
work_keys_str_mv AT mamasegaremabelmphahlele directonepotsynthesisofprimary4amino23diarylquinolinesviasuzukimiyauracrosscouplingof2aryl4azido3iodoquinolineswitharylboronicacids
AT malosejackmphahlele directonepotsynthesisofprimary4amino23diarylquinolinesviasuzukimiyauracrosscouplingof2aryl4azido3iodoquinolineswitharylboronicacids
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