A Class of Amide Ligands Enable Cu-Catalyzed Coupling of (Hetero)aryl Halides with Sulfinic Acid Salts under Mild Conditions

2018 ◽  
Vol 83 (12) ◽  
pp. 6589-6598 ◽  
Author(s):  
Jinlong Zhao ◽  
Songtao Niu ◽  
Xi Jiang ◽  
Yongwen Jiang ◽  
Xiaojing Zhang ◽  
...  
Keyword(s):  
Aryl Halides ◽  
Sulfinic Acid ◽  
Mild Conditions ◽  
Amide Ligands ◽  
Acid Salts

Iron(III)-Mediated Oxy-Sulfonylation of Enamides with Sodium and Lithium Sulfinates

2019 ◽  
Author(s):  
Philipp Kramer ◽  
Miro Halaczkiewicz ◽  
Yu Sun ◽  
Harald Kelm ◽  
Georg Manolikakes
Keyword(s):  
Sulfur Dioxide ◽  
Building Block ◽  
Sulfinic Acid ◽  
Biologically Relevant ◽  
Mild Conditions ◽  
Reaction Proceeds ◽  
Organolithium Chemistry ◽  
Direct Incorporation ◽  
Acid Salts

<p>An iron-mediated vicinal difunctionalization of enamides and enecarbamates with sulfinic acid salts and alcohols is described. This reaction proceeds under mild conditions and furnishes the oxy-sulfonylated products in moderate to excellent yields. Moreover, the direct incorporation of sulfur dioxide into the sulfonylated products via organolithium chemistry has been achieved. The formed <i>N</i>-<i>O</i>-acetals are competent acylimine precursors. Their utilization as building block for the synthesis of biologically relevant β-amidosulfones is described as well. <br></p>

Iron(III)-Mediated Oxy-Sulfonylation of Enamides with Sodium and Lithium Sulfinates

2019 ◽  
Author(s):  
Philipp Kramer ◽  
Miro Halaczkiewicz ◽  
Yu Sun ◽  
Harald Kelm ◽  
Georg Manolikakes
Keyword(s):  
Sulfur Dioxide ◽  
Building Block ◽  
Sulfinic Acid ◽  
Biologically Relevant ◽  
Mild Conditions ◽  
Reaction Proceeds ◽  
Organolithium Chemistry ◽  
Direct Incorporation ◽  
Acid Salts

<p>An iron-mediated vicinal difunctionalization of enamides and enecarbamates with sulfinic acid salts and alcohols is described. This reaction proceeds under mild conditions and furnishes the oxy-sulfonylated products in moderate to excellent yields. Moreover, the direct incorporation of sulfur dioxide into the sulfonylated products via organolithium chemistry has been achieved. The formed <i>N</i>-<i>O</i>-acetals are competent acylimine precursors. Their utilization as building block for the synthesis of biologically relevant β-amidosulfones is described as well. <br></p>

Chiral Mn(III) Salen Complex Immobilized on CuFe2O4@SiO2-NH2 NPs: A Cheap and Efficient Catalyst for N-arylation of Aryl Halides and Phenylboronic Acid Under Mild Conditions

2020 ◽  
Vol 17 (11) ◽  
pp. 857-863
Author(s):  
Mohammad Ali Nasseri ◽  
Seyyedeh Ameneh Alavi ◽  
Milad Kazemnejadi ◽  
Ali Allahresani
Keyword(s):  
Phenylboronic Acid ◽  
Significant Loss ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Efficient Catalyst ◽  
Aryl Chlorides ◽  
Mild Conditions ◽  
Cross Coupling Reactions ◽  
Salen Complex ◽  
Ft Ir

A convenient and efficient chiral CuFe2O4@SiO2-Mn(III) Ch.salen nanocatalyst has been developed for the C-N cross-coupling reactions of aryl halides/ phenylboronic acid with N-heterocyclic compounds in water and/or DMSO under mild conditions. The catalyst could be applied for the N-arylation of a variety of nitrogen-containing heterocycles with aryl chlorides, bromides, iodides and phenylboronic acid under mild conditions. Moderate to good yields were achieved for all substrates. The structure of catalyst was characterized using various techniques including FT-IR, FE-SEM, EDX, XRD, TEM and TGA. The catalyst can be simply recovered and reused for several times without significant loss of activity.

Borates as a Traceless Activation Group for Intermolecular Alkylarylation of Ethylene through Photoredox/Nickel Dual Catalysis

Synlett ◽  
2020 ◽  
Author(s):  
Shengqing Zhu ◽  
Lingling Chu ◽  
Xiaoliang Feng ◽  
Lei Guo
Keyword(s):  
Functional Groups ◽  
Aryl Halides ◽  
Nickel Catalysis ◽  
Mild Conditions ◽  
Dual Catalysis

AbstractA formal ethylene alkylarylation reaction with aryl halides and alkyl oxalates enabled by synergistic photoredox/nickel catalysis is reported. This protocol takes advantage of borates as a traceless activation group, achieving the formal ethylene difunctionalized products via a catalytic three-component 1,2-alkylarylation of vinyl borate followed by a base-assisted deborylation process. The mild conditions allow for excellent functional groups compatibility and broad substrate scope.

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