Electrochemically Enabled Chan–Lam Couplings of Aryl Boronic Acids and Anilines

Wexler, Ryan P.; Nuhant, Philippe; Senter, Timothy J.; Gale-Day, Zachary J.

doi:10.1021/acs.orglett.9b01434

Cited by 40 publications

(31 citation statements)

References 24 publications

(51 reference statements)

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“…In 2019, Gale-Day and co-workers reported the electrochemical synthesis of a variety of N-arylanilines via the Chan-Lam coupling of anilines and arylboronic acids utilizing a dual copper anode/cathode system in the presence of Et 3 N and air or oxygen (Scheme 29). 35 Anilines with electron-rich substituents or with para-halo groups reacted well, whereas those bearing electron-deficient groups gave moderate yields. A variety of arylboronic acids bearing both electron-withdrawing and -donating groups underwent the reaction smoothly to furnish the products in good to excellent yields.…”

Section: Scheme 27 Cu(oac) 2 -Mediated Reaction Of Arylboronic Acid Pmentioning

confidence: 99%

Advances in Carbon–Element Bond Construction under Chan–Lam Cross-Coupling Conditions: A Second Decade

et al. 2020

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Copper-mediated carbon–heteroatom bond-forming reactions involving a wide range of substrates have been in the spotlight for many organic chemists. This review highlights developments between 2010 and 2019 in both stoichiometric and catalytic copper-mediated reactions, and also examples of nickel-mediated reactions, under modified Chan–Lam cross-coupling conditions using various nucleophiles; examples include chemo- and regioselective N-arylations or O-arylations. The utilization of various nucleophiles as coupling partners together with reaction optimization (including the choice of copper source, ligands, base, and other additives), limitations, scope, and mechanisms are examined; these have benefitted the development of efficient and milder methods. The synthesis of medicinally valuable or pharmaceutically important nitrogen heterocycles, including isotope-labeled compounds, is also included. Chan–Lam coupling reaction can now form twelve different C–element bonds, making it one of the most diverse and mild reactions known in organic chemistry.1 Introduction2 Construction of C–N and C–O Bonds2.1 C–N Bond Formation2.1.1 Original Discovery via Stoichiometric Copper-Mediated C–N Bond Formation2.1.2 Copper-Catalyzed C–N Bond Formation2.1.3 Coupling with Azides, Sulfoximines, and Sulfonediimines as Nitrogen Nucleophiles2.1.4 Coupling with N,N-Dialkylhydroxylamines2.1.5 Enolate Coupling with sp3-Carbon Nucleophiles2.1.6 Nickel-Catalyzed Chan–Lam Coupling2.1.7 Coupling with Amino Acids2.1.8 Coupling with Alkylboron Reagents2.1.9 Coupling with Electron-Deficient Heteroarylamines2.1.10 Selective C–N Bond Formation for the Synthesis of Heterocycle-Containing Compounds2.1.11 Using Sulfonato-imino Copper(II) Complexes2.2 C–O Bond Formation2.2.1 Coupling with (Hetero)arylboron Reagents2.2.2 Coupling with Alkyl- and Alkenylboron Reagents3 C–Element (Element = S, P, C, F, Cl, Br, I, Se, Te, At) Bond Forma tion under Modified Chan–Lam Conditions4 Conclusions

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Section: Scheme 27 Cu(oac) 2 -Mediated Reaction Of Arylboronic Acid Pmentioning

confidence: 99%

Advances in Carbon–Element Bond Construction under Chan–Lam Cross-Coupling Conditions: A Second Decade

et al. 2020

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“…Intrigued by this previous report, 53 work in our lab focused on the application of electrochemical mediation to the traditional Chan-Lam reaction. 54 Specifically, the substrate scope focused on traditionally challenging electronpoor boronic acid coupling partners. Using inexpensive copper(II) acetate as the catalyst, good to excellent yields were achieved for a series of electron-poor boronic acids.…”

Section: Scheme 13 Electrochemical Synthesis Of Phenols and Aniline Umentioning

confidence: 99%

Recent Advances in Metal-Catalyzed, Electrochemical Coupling Reactions of sp2 Halides/Boronic Acids and sp3 Centers

Gale-Day¹

2020

Synthesis

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Traditionally, metal-catalyzed cross-coupling reactions rely on stable but expensive metals, such as palladium. However, the recent development of synthetic organic electrochemistry allows for in situ redox manipulations, expanding the use of cheaper, abundant and sustainable metals, such as nickel and copper as efficient cross-coupling catalysts. This short review covers the recent advances in metal-catalyzed electrochemical coupling reactions, with a focus on reactions of sp2 electrophiles and nucleophiles with sp3 coupling partners to form both C–C and C–heteroatom bonds.1 Introduction2 Nickel-Catalyzed C–C sp2–sp3 Coupling Reactions3 Coupling of Aryl Groups with Heteroatomic Nuclei4 Conclusion

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“…[ 16 ] Afterwards, Wexler et al reported an electrocatalytic coupling of arylboronic acids with amines by a dual copper anode/cathode system. [ 17 ] Soon after, copper‐catalyzed anaerobic Chan–Lam reaction between arylboronic acids and various amines with electrochemistry in replace of strong chemical oxidants was also achieved by Sevov's group. [ 18 ] Very recently, Di et al documented the coupling of 2‐aminopyridine and arylboronic acid to furnish N ‐arylpyridin‐2‐amine derivatives via irradiation of blue light using copper modified phosphorus‐doped g‐C 3 N 4 (Cu/P‐CN) as a heterogeneous photocatalyst.…”

Section: Introductionmentioning

confidence: 99%

Three copper(II) complexes derived from 2‐methylquinoline and cyclic secondary amines: Synthesis and catalytic application in C—N bond forming reactions

Jia

2022

Applied Organom Chemis

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Three copper(II) complexes (I-III) bearing N,O-bidentate ligands (L 1 -L 3 ), derived from 2-methylquinoline and cyclic secondary amines (including pyrrolidine, morpholine, and 4-methylpiperidine), were successfully prepared and successively employed in construction of C N bonds via the Chan-Lam coupling of 1H-imidazole derivatives with arylboronic acids. X-ray diffraction analysis demonstrated that the central copper(II) atom of II adopted the distorted tetrahedral geometry, which was four coordinated by one nitrogen atom and one oxygen atom from L 2 as well as two chloride atoms. Catalytic studies indicated that complex II displayed higher activity in Chan-Lam reaction than complex I or III. The present protocol for N,O-coordinated-copper complexcatalyzed C N coupling reaction exhibited some advantages such as wide scope of substrates, good yields, and mild conditions.

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Electrochemically Enabled Chan–Lam Couplings of Aryl Boronic Acids and Anilines

Cited by 40 publications

References 24 publications

Advances in Carbon–Element Bond Construction under Chan–Lam Cross-Coupling Conditions: A Second Decade

Advances in Carbon–Element Bond Construction under Chan–Lam Cross-Coupling Conditions: A Second Decade

Recent Advances in Metal-Catalyzed, Electrochemical Coupling Reactions of sp2 Halides/Boronic Acids and sp3 Centers

Three copper(II) complexes derived from 2‐methylquinoline and cyclic secondary amines: Synthesis and catalytic application in C—N bond forming reactions

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