Clean and fast cross-coupling of aryl halides in one-pot

Unsymmetrically coupled biaryls are synthesized in high yield starting from different aryl bromides and bis(pinacolato)diboron by carrying out the Miyaura borylation reaction followed by the Suzuki–Miyaura reaction in the same reaction pot over 1–2 mol % SiliaCat DPP-Pd. The SiliaCat DPP-Pd catalyst is air-stable and the method does not require the use of inert conditions. The use of non-toxic isopropanol or 2-butanol as reaction solvent further adds to the environmental benefits of this new green synthetic methodology.

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One-Pot Iridium Catalyzed C–H Borylation/Sonogashira Cross-Coupling: Access to Borylated Aryl Alkynes

Molecules ◽

10.3390/molecules25071754 ◽

2020 ◽

Vol 25 (7) ◽

pp. 1754 ◽

Cited By ~ 2

Author(s):

Ghayoor A. Chotana ◽

Jose R. Montero Bastidas ◽

Susanne L. Miller ◽

Milton R. Smith ◽

Robert E. Maleczka

Keyword(s):

Cross Coupling ◽

One Pot ◽

Aryl Bromides ◽

Aryl Alkynes

Borylated aryl alkynes have been synthesized via one-pot iridium catalyzed C–H borylation (CHB)/Sonogashira cross-coupling of aryl bromides. Direct borylation of aryl alkynes encountered problems related to the reactivity of the alkyne under CHB conditions. However, tolerance of aryl bromides to CHB made possible a subsequent Sonogashira cross-coupling to access the desired borylated aryl alkynes.

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ChemInform Abstract: Two-Step, One-Pot Ni-Catalyzed Neopentylglycolborylation and Complementary Pd/Ni-Catalyzed Cross-Coupling with Aryl Halides, Mesylates, and Tosylates.

ChemInform ◽

10.1002/chin.200912099 ◽

2009 ◽

Vol 40 (12) ◽

Author(s):

Daniela A. Wilson ◽

Christopher J. Wilson ◽

Brad M. Rosen ◽

Virgil Percec

Keyword(s):

Cross Coupling ◽

Aryl Halides ◽

One Pot

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The role of magnetic nanoparticles (MNP) as reducing agents in an MNP-supported Pd–catalyst for the reductive homocoupling of aryl halides

Canadian Journal of Chemistry ◽

10.1139/v11-133 ◽

2012 ◽

Vol 90 (1) ◽

pp. 138-144 ◽

Cited By ~ 8

Author(s):

Jie Zheng ◽

Shengyue Lin ◽

Bi-Wang Jiang ◽

Todd B. Marder ◽

Zhen Yang

Keyword(s):

Magnetic Nanoparticles ◽

Aryl Halide ◽

Reducing Power ◽

Cross Coupling ◽

Reducing Agent ◽

Aryl Halides ◽

Pd Catalyst ◽

Reductive Homocoupling ◽

Supported Pd

A palladium pincer catalyst grafted onto the surface of magnetic nanoparticles (MNPs) has been developed. This material effectively catalyzes the reductive homocoupling of various aryl halide substrates, with the MNP support acting as the reducing agent. The catalyst can be recycled up to five times in the absence of additional reducing agent to give almost quantitative yields of biaryl homocoupling products. After the reducing power of the MNP has been depleted, the supported Pd complex remains an effective catalyst for Suzuki–Miyaura cross-coupling.

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Recent Progress in the Cross-Coupling Reaction Using Triorganosilyl-Type Reagents

Synlett ◽

10.1055/s-0036-1589008 ◽

2017 ◽

Vol 28 (15) ◽

pp. 1873-1884 ◽

Cited By ~ 6

Author(s):

Yasunori Minami ◽

Tamejiro Hiyama ◽

Takeshi Komiyama

Keyword(s):

Recent Progress ◽

Coupling Reaction ◽

Cross Coupling ◽

Aryl Halides ◽

Organosilicon Compounds ◽

Aryl Bromides ◽

Cross Coupling Reaction ◽

The Cross ◽

Silicon Based ◽

Coupling Polymerization

The silicon-based cross-coupling reaction has attracted much attention over recent decades because there are many advantages in using organosilicon compounds. However, the use of reagents with a triorganosilyl group as a key function remains to be established. This account summarizes our recent progress in cross-coupling chemistry with such silyl reagents.1 Introduction2 Preparation of HOMSi Reagents from Aryl Bromides and Disilanes3 HOMSi Reagents from Heteroaromatics and Hydrosilanes4 Cross-Coupling Polymerization with HOMSi Reagents5 Cross-Coupling with Aryl(triethyl)silanes6 Amination of Aryl Halides with N-TMS-Amines7 Conclusion and Perspective

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One-pot Synthesis of Dibenzofurans via SNAr and Subsequent Ligand-free Palladium-catalyzed Intramolecular Aryl-aryl Cross-coupling Reactions under Microwave Irradiation

Zeitschrift für Naturforschung B ◽

10.1515/znb-2011-0808 ◽

2011 ◽

Vol 66 (8) ◽

pp. 833-836

Author(s):

Zhiping Che ◽

Hui Xu

Keyword(s):

Microwave Irradiation ◽

Cross Coupling ◽

Aryl Halides ◽

Coupling Reactions ◽

One Pot ◽

One Pot Synthesis ◽

Cross Coupling Reactions ◽

Ligand Free ◽

Palladium Catalyzed ◽

Snar Reaction

An efficient one-pot synthesis of dibenzofurans, via SNAr reaction of aryl halides and ortho-bromophenols in the presence of anhydrous K2CO3 and subsequent ligand-free palladium-catalyzed intramolecular aryl-aryl cross-coupling cyclization under microwave irradiation, is described.

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A facile and convenient sequential homobimetallic catalytic approach towards β-methylstyrenes. A one-pot Stille cross-coupling/isomerization strategy

Organic & Biomolecular Chemistry ◽

10.1039/c4ob00604f ◽

2014 ◽

Vol 12 (22) ◽

pp. 3735-3743 ◽

Cited By ~ 7

Author(s):

Sebastián O. Simonetti ◽

Enrique L. Larghi ◽

Teodoro S. Kaufman

Keyword(s):

Double Bond ◽

Coupling Reaction ◽

Cross Coupling ◽

Aryl Halides ◽

One Pot ◽

Cross Coupling Reaction

A one-pot approach towards β-methylstyrenes is reported. The transformation involves a Stille cross-coupling reaction of aryl halides with allyltributylstannane, followed by an in situ Pd-catalyzed double bond conjugative migration.

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