Synthesis of new functionalized triarylmethanes via Suzuki cross-coupling and Heck-type vinylation reactions

A novel class of triarylmethanes (TRAMs) containing one or two biaryl moieties was synthesized efficiently through the $\mathrm{Pd}(\mathrm{PPh}_{3})_{4}$-catalyzed Suzuki–Miyaura cross-coupling reaction of brominated TRAMs with arylboronic acid derivatives. We also demonstrate that brominated TRAMs...

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Published in:Comptes Rendus. Chimie
Main Authors: Mohammadiannejad, Kazem, Hosseini, Raziyeh, Ranjbar-Karimi, Reza
Format: Article
Language:English
Published: Académie des sciences 2020-11-01
Subjects:
Online Access:https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.34/
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author Mohammadiannejad, Kazem
Hosseini, Raziyeh
Ranjbar-Karimi, Reza
author_facet Mohammadiannejad, Kazem
Hosseini, Raziyeh
Ranjbar-Karimi, Reza
author_sort Mohammadiannejad, Kazem
collection DOAJ
container_title Comptes Rendus. Chimie
description A novel class of triarylmethanes (TRAMs) containing one or two biaryl moieties was synthesized efficiently through the $\mathrm{Pd}(\mathrm{PPh}_{3})_{4}$-catalyzed Suzuki–Miyaura cross-coupling reaction of brominated TRAMs with arylboronic acid derivatives. We also demonstrate that brominated TRAMs can be efficiently functionalized via a one-pot, two-step Pd-catalyzed Heck-type process. This protocol provides convenient access to diverse vinylated TRAMs that are generally not obtained by using the common synthetic methods for TRAMs.
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spelling doaj-art-ca2acf89fbaf40dd92aa9cfe8d91b65e2025-08-20T00:10:02ZengAcadémie des sciencesComptes Rendus. Chimie1878-15432020-11-01236-736337410.5802/crchim.3410.5802/crchim.34Synthesis of new functionalized triarylmethanes via Suzuki cross-coupling and Heck-type vinylation reactionsMohammadiannejad, Kazem0https://orcid.org/0000-0001-6383-8052Hosseini, Raziyeh1https://orcid.org/0000-0002-7178-7467Ranjbar-Karimi, Reza2https://orcid.org/0000-0002-2599-7252NMR Laboratory, Faculty of Science, Vali-e-Asr University of Rafsanjan, Rafsanjan, 77176, Islamic Republic of IranDepartment of Chemistry, Faculty of Science, Vali-e-Asr University of Rafsanjan, Rafsanjan, 77176, Islamic Republic of IranDepartment of Chemistry, Faculty of Science, Vali-e-Asr University of Rafsanjan, Rafsanjan, 77176, Islamic Republic of IranA novel class of triarylmethanes (TRAMs) containing one or two biaryl moieties was synthesized efficiently through the $\mathrm{Pd}(\mathrm{PPh}_{3})_{4}$-catalyzed Suzuki–Miyaura cross-coupling reaction of brominated TRAMs with arylboronic acid derivatives. We also demonstrate that brominated TRAMs can be efficiently functionalized via a one-pot, two-step Pd-catalyzed Heck-type process. This protocol provides convenient access to diverse vinylated TRAMs that are generally not obtained by using the common synthetic methods for TRAMs.https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.34/TriarylmethanesC–C bond formationPalladium catalysisSuzuki–Miyaura cross-coupling reactionsHeck-type reactions
spellingShingle Mohammadiannejad, Kazem
Hosseini, Raziyeh
Ranjbar-Karimi, Reza
Synthesis of new functionalized triarylmethanes via Suzuki cross-coupling and Heck-type vinylation reactions
Triarylmethanes
C–C bond formation
Palladium catalysis
Suzuki–Miyaura cross-coupling reactions
Heck-type reactions
title Synthesis of new functionalized triarylmethanes via Suzuki cross-coupling and Heck-type vinylation reactions
title_full Synthesis of new functionalized triarylmethanes via Suzuki cross-coupling and Heck-type vinylation reactions
title_fullStr Synthesis of new functionalized triarylmethanes via Suzuki cross-coupling and Heck-type vinylation reactions
title_full_unstemmed Synthesis of new functionalized triarylmethanes via Suzuki cross-coupling and Heck-type vinylation reactions
title_short Synthesis of new functionalized triarylmethanes via Suzuki cross-coupling and Heck-type vinylation reactions
title_sort synthesis of new functionalized triarylmethanes via suzuki cross coupling and heck type vinylation reactions
topic Triarylmethanes
C–C bond formation
Palladium catalysis
Suzuki–Miyaura cross-coupling reactions
Heck-type reactions
url https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.34/
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AT hosseiniraziyeh synthesisofnewfunctionalizedtriarylmethanesviasuzukicrosscouplingandhecktypevinylationreactions
AT ranjbarkarimireza synthesisofnewfunctionalizedtriarylmethanesviasuzukicrosscouplingandhecktypevinylationreactions