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- Title
Chan–Lam N-Arylation of Adamantane-Containing Amines.
- Authors
Kuliukhina, D. S.; Malysheva, A. S.; Averin, A. D.; Savelyev, E. N.; Orlinson, B. S.; Novakov, I. A.; Beletskaya, I. P.
- Abstract
The Chan–Lam reaction conditions were optimized for the synthesis of N-aryl derivatives of adamantane-containing amines. A number of adamantane-containing amines and diamines with different steric hindrances at the primary amino groups were reacted with p-tolylboronic acid under the optimized conditions [0.1 M solution of amine in MeCN, p-tolylboronic acid (2 equiv), DBU (2 equiv), copper(II) acetate (20 mol %), 25°C, 24 h]. The reactivity of the amines was found to strongly depend on their structure, and the maximum yield of the target products reached 74% from the monoamines and 66% from the diamines.
- Subjects
ADAMANTANE derivatives; DIAMINES; AMINES; AMINO group; COPPER; STERIC hindrance; AMINE derivatives
- Publication
Russian Journal of Organic Chemistry, 2023, Vol 59, Issue 12, p2107
- ISSN
1070-4280
- Publication type
Article
- DOI
10.1134/S1070428023120072