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Synfacts 2022; 18(07): 0772
DOI: 10.1055/s-0041-1737636
Metals in Synthesis

The Chan–Evans–Lam Coupling

Contributor(s):
Martin Oestreich
,
Hendrik F. T. Klare
,
Lucie Finck
Lam PY. S, *, Clark CG, Saubern S, Adams J, Winters MP, Chan DM. T, *, Combs A. The DuPont Merck Pharmaceutical Company, Wilmington, USA
New Aryl/Heteroaryl C–N Bond Cross-coupling Reactions via Arylboronic Acid/Cupric Acetate Arylation.

Tetrahedron Lett. 1998;
39: 2941-2944
DOI: 10.1016/S0040-4039(98)00504-8.
CrossrefGoogle Scholar
Chan DM. T, *, Monaco KL, Wang R.-P, Winters MP. Stine-Haskell Research Center DuPont, Newark, USA
New N- and O-Arylations with Phenylboronic Acids and Cupric Acetate.

Tetrahedron Lett. 1998;
39: 2933-2936
DOI: 10.1016/S0040-4039(98)00503-6.
CrossrefGoogle Scholar
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Key words

aryl amines - arylboronic acids - aryl ethers - copper - cross-coupling

Significance

In 1998, Chan and Lam as well as Evans (Tetrahedron Lett. 1998, 39, 2937) independently reported a copper(II)-promoted oxidative cross-coupling of aryl boronic acids and ­heteroatomic nucleophiles such as amines and ­alcohols to form C(sp2)–heteroatom bonds. The ­reaction proceeds with stoichiometric amounts of copper under oxidative conditions (air or O2) at room temperature.


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Comment

Over the past decades, the Chan–­Evans–Lam coupling has been thoroughly investigated and reaction conditions were significantly enhanced to turn this reaction into a catalytic process. C(sp2)–S, C(sp2)–P and C(sp2)–halogen bond formations have been achieved. Studies for the elucidation of the mechanism have been recently described (J. C. Vantourout et al. J. Am. Chem. Soc. 2017, 139, 4769).


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Publication History

Article published online:
15 June 2022

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