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

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 mediated

Publication History

Received: 21 July 2020

Accepted after revision: 12 October 2020

Article published online:
15 December 2020

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