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Synthesis 2021; 53(05): 805-847
DOI: 10.1055/s-0040-1705971
DOI: 10.1055/s-0040-1705971
review
Advances in Carbon–Element Bond Construction under Chan–Lam Cross-Coupling Conditions: A Second Decade
This research work was financially supported by DST-SERB (EMR/2017/002533) .
In memory of Siva Reddy
Abstract
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 sp3-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
Key words
Chan–Lam coupling - C–O bond formation - C–N bond formation - N-arylation - copper-catalyzed - copper mediatedPublication History
Received: 21 July 2020
Accepted after revision: 12 October 2020
Article published online:
15 December 2020
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For selected general reviews, see:
For reviews on the Chan–Lam coupling, see:
Two reviews (1k and 1l) were published during the final stage of our manuscript preparation, see: