One-Pot Homo- and Cross-Coupling Reactions of Arenediazonium Tosylate Salts for the Synthesis of Biaryls and Polyaryls

Vajpayee, Vaishali; Song, Young Ho; Ahn, Jeong Soo; Chi, Ki‐Whan

doi:10.5012/bkcs.2011.32.8.2970

Bulletin of the Korean Chemical Society

2011

DOI: 10.5012/bkcs.2011.32.8.2970

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One-Pot Homo- and Cross-Coupling Reactions of Arenediazonium Tosylate Salts for the Synthesis of Biaryls and Polyaryls

Vaishali Vajpayee¹,

Young Ho Song²,

Jeong Soo Ahn³

et al.

Abstract: One-pot homo-and cross-coupling reactions of arenediazonium tosylate salts bearing a halogen group have been exploited for the synthesis of biaryls and polyaryls under mild conditions. Pd(OAc) 2 has proven to be an efficient catalyst for the successful dual transformation of diazonium salts into p-quaterphenyl (3).

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Cited by 7 publications

References 25 publications

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Assembling of Polyaryls (Terphenyls, Tetraphenyls, Pentaphenyls, and Hexaphenyls) through Pd(II)‐catalyzed C−H Arylation of Biaryl Carboxamides with Iodobiaryls

Dalal,

Babu,

Banga

2023

Asian J Org Chem

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A wide range of polyaryl compounds (π‐extended biaryls) including terphenyls, tetraphenyls, pentaphenyls, and hexaphenyls were assembled in a single operation of Pd(II)‐catalyzed C−H coupling of biaryl carboxamides and iodobiaryls. Traditionally, cross‐coupling protocols involving organometallic reagents were employed to assemble the core structure of π‐extended biaryls (polyphenylenes or polyaryls). The pre‐assembling of organometallic reagents is a limitation in investigations pertaining to the aryl‐aryl cross‐coupling reactions affording polyaryls (polyphenylenes). We report the application of Pd(II)‐catalyzed bidentate directing group (DG)‐aided C−H arylation method for constructing polyaryl motifs (π‐extended biaryls) using biaryl‐based carboxamides and iodobiaryls as the coupling partners in a single operation. The current investigation on the bidentate DG‐aided C−H arylation of biaryl carboxamides with iodobiaryls is expected to serve as a useful route to enrich the library of π‐extended biaryls (polyphenylenes or polyaryls).

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Assembling of Polyaryls (Terphenyls, Tetraphenyls, Pentaphenyls, and Hexaphenyls) through Pd(II)‐catalyzed C−H Arylation of Biaryl Carboxamides with Iodobiaryls

Dalal,

Babu,

Banga

2023

Asian J Org Chem

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Rapid Synthesis of Thiophene‐Based, Organic Dyes for Dye‐Sensitized Solar Cells (DSSCs) by a One‐Pot, Four‐Component Coupling Approach

Matsumura¹,

Maitani²,

Wada³

et al. 2015

Chemistry A European J

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This one-pot, four-component coupling approach (Suzuki-Miyaura coupling/C-H direct arylation/Knoevenagel condensation) was developed for the rapid synthesis of thiophene-based organic dyes for dye-sensitized solar cells (DSSCs). Seven thiophene-based, organic dyes of various donor structures with/without the use of a 3,4-ethylenedioxythiophene (EDOT) moiety were successfully synthesized in good yields based on a readily available thiophene boronic acid pinacol ester scaffold (one-pot, 3-step, 35-61%). Evaluation of the photovoltaic properties of the solar cells that were prepared using the synthesized dyes revealed that the introduction of an EDOT structure beside a cyanoacrylic acid moiety improved the short-circuit current (Jsc) while decreasing the fill factor (FF). The donor structure significantly influenced the open-circuit voltage (Voc), the FF, and the power conversion efficiency (PCE). The use of a n-hexyloxyphenyl amine donor, and our originally developed, rigid, and nonplanar donor, both promoted good cell performance (η=5.2-5.6%).

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Synthesis, Structure, and Synthetic Potential of Arenediazonium Trifluoromethanesulfonates as Stable and Safe Diazonium Salts

et al. 2018

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Aromatic diazonium salts are valuable building blocks for organic synthesis; however, in most cases, they are unstable, unsafe, poorly soluble, and/or expensive. In this paper, we have shown that a variety of stable and safe arenediazonium triflates ArN2+ TfO– can be obtained easily and in high yields by diazotization of anilines with tert‐butyl nitrite in the presence of trifluoromethanesulfonic acid. Arenediazonium triflates are relatively shelf‐stable in the dry state. They dissolve well in water, as well as polar and even nonpolar organic solvents. Less than 800 J/g of energy is released during the thermal decomposition of these salts, which indicates their explosion safety. Arenediazonium triflates have a high reactivity in the known reactions of diazonium chemistry, and undergo an unusual metal‐free chlorodediazonization reaction with chloroform and CCl4.

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One-Pot Homo- and Cross-Coupling Reactions of Arenediazonium Tosylate Salts for the Synthesis of Biaryls and Polyaryls

Cited by 7 publications

References 25 publications

Assembling of Polyaryls (Terphenyls, Tetraphenyls, Pentaphenyls, and Hexaphenyls) through Pd(II)‐catalyzed C−H Arylation of Biaryl Carboxamides with Iodobiaryls

Assembling of Polyaryls (Terphenyls, Tetraphenyls, Pentaphenyls, and Hexaphenyls) through Pd(II)‐catalyzed C−H Arylation of Biaryl Carboxamides with Iodobiaryls

Rapid Synthesis of Thiophene‐Based, Organic Dyes for Dye‐Sensitized Solar Cells (DSSCs) by a One‐Pot, Four‐Component Coupling Approach

Synthesis, Structure, and Synthetic Potential of Arenediazonium Trifluoromethanesulfonates as Stable and Safe Diazonium Salts

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