Copper(II)‐Catalyzed C–S Cross‐Coupling with Thiazolidine‐2‐thiones and Boronic Acids: Synthesis of Azole Sulfides

Shanmugapriya, Jayabalan; Rajaguru, Kandasamy; Muthusubramanian, Shanmugam; Bhuvanesh, Nattamai

doi:10.1002/ejoc.201600160

Cited by 24 publications

(10 citation statements)

References 83 publications

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“…Heterocyclic thiols and thiones are useful precursors for C–S bond-forming reactions . Heterocyclic thiols and thiones have been extensively used for the formation of C–S bonds, whereas their utility for the formation of C–N bonds are rare .…”

Section: Introductionmentioning

confidence: 99%

Iodine-Catalyzed Chemoselective C–N Bond-Forming Reactions Using Benzylic or Cinnamyl Alcohols with Heterocyclic Thiols and Thiones

Siddaraju

Prabhu

2018

J. Org. Chem.

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A chemoselective formation of C-N bond catalyzed by iodine has been developed using heterocyclic thiols and thiones. The reaction occurs at the nitrogen center over the sulfur, leading to the amination against the traditional sulfenylation. A wide variety of allylic and benzylic alcohols serve as coupling partners. This method showed a good tolerance toward 1 H-tetrazole-5-thiol, 5-methyl-1,3,4-thiadiazole-2-thiol, benzo[ d]thiazole-2(3 H)-thione, and benzo[ d]oxazole-2(3 H)-thione derivatives.

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Section: Introductionmentioning

confidence: 99%

Iodine-Catalyzed Chemoselective C–N Bond-Forming Reactions Using Benzylic or Cinnamyl Alcohols with Heterocyclic Thiols and Thiones

Siddaraju

Prabhu

2018

J. Org. Chem.

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“…Different 2-mercaptobenzothiazoles 51a – n can be readily prepared from the easily available 2-halogenoanilines and potassium xanthogenate ( Scheme 43 ). Compounds 51a – c prepared in [ 101 ] were subjected to cross-coupling with aryl boronic acids in dichloroethane (DCE) in the presence of Cu(acac) 2 ( Scheme 43 , upper reaction). The method is characterized by mild conditions, the absence of additional ligand, short reaction time and good yield.…”

Section: 2-mercaptobenzothiazolesmentioning

confidence: 99%

Modern Approaches to the Synthesis and Transformations of Practically Valuable Benzothiazole Derivatives

2021

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The review is devoted to modern trends in the chemistry of 2-amino and 2-mercapto substituted benzothiazoles covering the literature since 2015. The reviewed heterocycles belong to biologically active and industrially demanded compounds. Newly developed synthesis methods can be divided into conventional multistep processes and one-pot, atom economy procedures, realized using green chemistry principles and simple reagents. The easy functionalization of the 2-NH2 and 2-SH groups and the benzene ring of the benzothiazole moiety allows considering them as highly reactive building blocks for organic and organoelement synthesis, including the synthesis of pharmacologically active heterocycles. The review provides a summary of findings, which may be useful for developing new drugs and materials and new synthetic approaches and patterns of reactivity.

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“…99 In 2016, Muthusubramanian and co-workers reported the Cu(II)-catalyzed C-S cross-coupling of thiazolidine-2thiones with boronic acids using Cu(acac) 2 in DCE to give azole sulfides under base-, ligand-, and additive-free conditions and requiring shorter reactions times (Scheme 120); one example of the corresponding reaction of an oxazolidine-2-thione was reported. 100 Azole sulfides find applications in the biological, pharmaceutical, and materials fields. The first multicomponent reaction (MCR) was explored by Zhao and co-workers in 2016, which involved arylboronic acids, elemental sulfur, and P(O)H compounds.…”

Section: Review Synthesismentioning

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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Copper(II)‐Catalyzed C–S Cross‐Coupling with Thiazolidine‐2‐thiones and Boronic Acids: Synthesis of Azole Sulfides

Cited by 24 publications

References 83 publications

Iodine-Catalyzed Chemoselective C–N Bond-Forming Reactions Using Benzylic or Cinnamyl Alcohols with Heterocyclic Thiols and Thiones

Iodine-Catalyzed Chemoselective C–N Bond-Forming Reactions Using Benzylic or Cinnamyl Alcohols with Heterocyclic Thiols and Thiones

Modern Approaches to the Synthesis and Transformations of Practically Valuable Benzothiazole Derivatives

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

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