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
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
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.
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).
