Advances in Carbon-Element Bond Construction under Chan-Lam Cross-Coupling Conditions: A Second Decade
- Title
- Advances in Carbon-Element Bond Construction under Chan-Lam Cross-Coupling Conditions: A Second Decade
- Creator
- Vijayan A.; Rao D.N.; Radhakrishnan K.V.; Lam P.Y.S.; Das P.
- Description
- 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 Introduction 2 Construction of C-N and C-O Bonds 2.1 C-N Bond Formation 2.1.1 Original Discovery via Stoichiometric Copper-Mediated C-N Bond Formation 2.1.2 Copper-Catalyzed C-N Bond Formation 2.1.3 Coupling with Azides, Sulfoximines, and Sulfonediimines as Nitrogen Nucleophiles 2.1.4 Coupling with N, N -Dialkylhydroxylamines 2.1.5 Enolate Coupling with sp 3-Carbon Nucleophiles 2.1.6 Nickel-Catalyzed Chan-Lam Coupling 2.1.7 Coupling with Amino Acids 2.1.8 Coupling with Alkylboron Reagents 2.1.9 Coupling with Electron-Deficient Heteroarylamines 2.1.10 Selective C-N Bond Formation for the Synthesis of Heterocycle-Containing Compounds 2.1.11 Using Sulfonato-imino Copper(II) Complexes 2.2 C-O Bond Formation 2.2.1 Coupling with (Hetero)arylboron Reagents 2.2.2 Coupling with Alkyl- and Alkenylboron Reagents 3 C-Element (Element = S, P, C, F, Cl, Br, I, Se, Te, At) Bond Forma tion under Modified Chan-Lam Conditions 4 Conclusions. 2021 Georg Thieme Verlag. All rights reserved.
- Source
- Synthesis (Germany), Vol-53, No. 5, pp. 805-847.
- Date
- 2021-01-01
- Publisher
- Georg Thieme Verlag
- Subject
- C-N bond formation; C-O bond formation; Chan-Lam coupling; copper mediated; copper-catalyzed; N-arylation
- Coverage
- Vijayan A., Department of Chemistry, CHRIST, Deemed to Be University, Hosur road, Bengaluru, 560029, India, CSIR, National Institute for Interdisciplinary Science and Technology, Industrial Estate PO, Thiruvananthapuram, 695019, India; Rao D.N., Department of Chemistry, Indian Institute of Technology (ISM), Dhanbad, 826004, India; Radhakrishnan K.V., CSIR, National Institute for Interdisciplinary Science and Technology, Industrial Estate PO, Thiruvananthapuram, 695019, India; Lam P.Y.S., Baruch S. Blumberg Institute, Doylestown, 18902, PA, United States; Das P., Department of Chemistry, Indian Institute of Technology (ISM), Dhanbad, 826004, India
- Rights
- Restricted Access
- Relation
- ISSN: 397881; CODEN: SYNTB
- Format
- Online
- Language
- English
- Type
- Review
Collection
Citation
Vijayan A.; Rao D.N.; Radhakrishnan K.V.; Lam P.Y.S.; Das P., “Advances in Carbon-Element Bond Construction under Chan-Lam Cross-Coupling Conditions: A Second Decade,” CHRIST (Deemed To Be University) Institutional Repository, accessed February 23, 2025, https://archives.christuniversity.in/items/show/21615.