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      Nucleophilic C4-selective (hetero) arylation of pyridines for facile synthesis of heterobiaryls

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          Abstract

          The synthesis of heterobiaryl compounds holds significant value in organic chemistry due to their extensive range of applications. Herein, we report a highly efficient strategy for conducting C4-selective (hetero) arylation of pyridines using N-aminopyridinium salts. The reaction proceeds readily at room temperature in the presence of a base, thus eliminating the requirement for catalysts or oxidants. This method allows for the installation of various electron-rich (hetero) aryl groups on pyridines, resulting in the streamlined synthesis of highly valuable C4-(hetero) aryl pyridine derivatives, which are otherwise challenging to acquire via conventional methods. This simple and straightforward method will facilitate access to a range of heterobiaryl compounds thereby promoting their application in various scientific disciplines.

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          Most cited references47

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          Analysis of the structural diversity, substitution patterns, and frequency of nitrogen heterocycles among U.S. FDA approved pharmaceuticals.

          Nitrogen heterocycles are among the most significant structural components of pharmaceuticals. Analysis of our database of U.S. FDA approved drugs reveals that 59% of unique small-molecule drugs contain a nitrogen heterocycle. In this review we report on the top 25 most commonly utilized nitrogen heterocycles found in pharmaceuticals. The main part of our analysis is divided into seven sections: (1) three- and four-membered heterocycles, (2) five-, (3) six-, and (4) seven- and eight-membered heterocycles, as well as (5) fused, (6) bridged bicyclic, and (7) macrocyclic nitrogen heterocycles. Each section reveals the top nitrogen heterocyclic structures and their relative impact for that ring type. For the most commonly used nitrogen heterocycles, we report detailed substitution patterns, highlight common architectural cores, and discuss unusual or rare structures.
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            Direct C-H arylation of electron-deficient heterocycles with arylboronic acids.

            A direct arylation of a variety of electron-deficient heterocycles with arylboronic acids has been developed. This new reaction proceeds readily at room temperature using inexpensive reagents: catalytic silver(I) nitrate in the presence of persulfate co-oxidant. The scope with respect to heterocycle and boronic acid coupling partner is broad, and sensitive functional groups are tolerated. This method allows for rapid access to a variety of arylated heterocycles that would be more difficult to access with traditional methods.
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              Visible Light-mediated Direct Arylation of Arenes and Heteroarenes Using Diaryliodonium Salts in the Presence and Absence of a Photocatalyst

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                Author and article information

                Contributors
                Journal
                Front Chem
                Front Chem
                Front. Chem.
                Frontiers in Chemistry
                Frontiers Media S.A.
                2296-2646
                01 September 2023
                2023
                : 11
                : 1254632
                Affiliations
                [1] 1 Department of Chemistry , Korea Advanced Institute of Science and Technology (KAIST) , Daejeon, Republic of Korea
                [2] 2 Center for Catalytic Hydrocarbon Functionalizations , Institute for Basic Science (IBS) , Daejeon, Republic of Korea
                Author notes

                Edited by: Takashi Ohshima, Kyushu University, Japan

                Reviewed by: Tao Shi, The Scripps Research Institute, United States

                Matsubara Ryosuke, Kobe University, Japan

                Jin Kyoon Park, Pusan National University, Republic of Korea

                *Correspondence: Sungwoo Hong, hongorg@ 123456kaist.ac.kr
                Article
                1254632
                10.3389/fchem.2023.1254632
                10502421
                37720719
                4eeeeed2-4851-4d3c-a851-4a60e68c5dde
                Copyright © 2023 Kim, You and Hong.

                This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.

                History
                : 07 July 2023
                : 17 August 2023
                Funding
                This research was supported financially by Institute for Basic Science (IBS-R010-A2).
                Categories
                Chemistry
                Original Research
                Custom metadata
                Organic Chemistry

                c-h (hetero) arylation,pyridinium salt,c4-selectivity,heterobiaryl,metal-free

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