Photoinduced inverse Sonogashira coupling reaction

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Visible-Light-Promoted Formation of C-C and C-P Bonds Derived from Evolution of Bromoalkynes under Additive-Free Conditions: Synthesis of 1,1-Dibromo-1-en-3-ynes and Alkynylphosphine Oxides

Hailong Xu et al.

Summary: The controllable achievement of C-C and C-P bond formations is developed via visible-light-promoted bromoalkyne dimerization or its further transformation with secondary phosphine oxides.

CHINESE JOURNAL OF CHEMISTRY (2021)

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Article Chemistry, Organic

Decatungstate as Direct Hydrogen Atom Transfer Photocatalyst for SOMOphilic Alkynylation

Luca Capaldo et al.

Summary: A versatile approach for alkynylation of various aliphatic hydrogen donors including alkanes was achieved using tetrabutylammonium decatungstate as a photocatalyst. The reaction mechanism involved generating organoradicals from C-H/Si-H bonds followed by SOMOphilic alkynylation to form internal alkynes. The impact of different radicofugal groups on the reaction outcome was evaluated through experimental and computational methods.

ORGANIC LETTERS (2021)

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Article Chemistry, Applied

Catalyst-Free Csp-Csp3 Cross-Coupling of Bromodifluoroacetamides with 1-Iodoalkynes under Visible-Light Irradiation

Yoshihiko Yamamoto et al.

Summary: This study demonstrates a cross-coupling reaction between bromodifluoroacetamides and (iodoethynyl)arenes without the need for a photocatalyst under visible light conditions. The reaction proceeds through the homolysis of bromodifluoroacetamides and coupling with 1-iodoalkynes via a radical chain process, leading to various organofluorine compounds. The developed photo-coupling method shows synthetic utility in the divergent transformations of the coupling products.

ADVANCED SYNTHESIS & CATALYSIS (2021)

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Article Chemistry, Multidisciplinary

Direct Photoexcitation of Ethynylbenziodoxolones: An Alternative to Photocatalysis for Alkynylation Reactions**

Stephanie G. E. Amos et al.

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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Physical

Selective C(sp3)-C(sp3) Cleavage/Alkynylation of Cycloalkylamides Enables Aminoalkyne Synthesis with Hypervalent Iodine Reagents

Zhengyi Liu et al.

Summary: A selective C(sp(3))-C(sp(3)) cleavage/alkynylation of cycloalkylamides for aminoalkyne synthesis was reported under mild photoredox catalysis. γ- and δ-Aminoalkynes with diverse alkyne and amine substituents were efficiently constructed via amidyl radicals enabled by hypervalent iodine(III) reagents. Catalytic cyclic iodine(III) BI'-OAc facilitated the single-electron oxidation and ring-opening alkynylation of cycloalkylamides.

ACS CATALYSIS (2021)

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Review Chemistry, Organic

SOMOphilic alkynylation using acetylenic sulfones as functional reagents

Danhua Ge et al.

Summary: This review provides an overview of recent advancements in alkynylation using acetylenic sulfones, highlighting their role in the synthesis of alkynes, fluoroalkylated compounds, sulfonylated compounds, and in situ SO2 capture. The article discusses direct alkynylation with various C-centered radicals and multi-step reaction modes involving acetylenic sulfones, while emphasizing the generality of substrate scope and proposed mechanisms.

ORGANIC CHEMISTRY FRONTIERS (2021)

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Article Chemistry, Organic

Visible-Light-Induced Alkynylation of α-C-H Bonds of Ethers with Alkynyl Bromides without External Photocatalyst

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CHEMISTRY-A EUROPEAN JOURNAL (2020)

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Nickel-Catalyzed Sonogashira C(sp)-C(sp2) Coupling through Visible-Light Sensitization

Da-Liang Zhu et al.

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Photocatalytic Umpolung of N- and O-substituted alkenes for the synthesis of 1,2-amino alcohols and diols

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CHEMICAL SCIENCE (2020)

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Kinetic investigation of thermal and photoinduced homolysis of alkylated verdazyls

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Abhishek Dewanji et al.

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Gold- or Indium-Catalyzed Cross-Coupling of Bromoalkynes with Allylsilanes through a Concealed Rearrangement

M. Elena de Orbe et al.

ACS CATALYSIS (2019)

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A BODIPY- functionalized PdII photoredox catalyst for Sonogashira C- C cross- coupling reactions

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Photoinduced Copper-Catalyzed Coupling of Terminal Alkynes and Alkyl Iodides

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CHEMICAL SCIENCE (2018)

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Broad-Scope Rh-Catalyzed Inverse-Sonogashira Reaction Directed by Weakly Coordinating Groups

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ACS CATALYSIS (2018)

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Photoinduced Remote Functionalization of Amides and Amines Using Electrophilic Nitrogen Radicals

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Transition-Metal-Free Alkynylation of 2-Oxindoles through Radical-Radical Coupling

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Direct cross-coupling of aryl alkynyliodines with arylsulfinic acids leading to alkynyl sulfones under catalyst-free conditions

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Titanium dioxide visible light photocatalysis: surface association enables photocatalysis with visible light irradiation

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Experimental and Calculated Electrochemical Potentials of Common Organic Molecules for Applications to Single-Electron Redox Chemistry

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Halogen Bonding of (Iodoethynyl)benzene Derivatives in Solution

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Photo-Induced Sonogashira C-C Coupling Reaction Catalyzed by Simple Copper(I) Chloride Salt at Room Temperature

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Photoinduced C-Br homolysis of 2-bromobenzophenones and pschorr ring closure of 2-aroylaryl radicals to fluorenones

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Photoinduced inverse Sonogashira coupling reaction

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