Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume -, Issue -, Pages -Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c00700
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Funding
- Natural Science Foundation of Xinjiang Uygur Autonomous Region [2021D01A115]
- National Natural Science Foundation of China [21762044]
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A TEMPO-promoted method for the synthesis of symmetric bis-N-Mannich bases via sequential activation of two alpha,alpha'-amino C(sp3)-H bonds of N,N-dimethylanilines under mild conditions is developed. This methodology is further extended for monoimidation of alpha-amino-functionalized methylanilines to give unsymmetric N-Mannich bases in good to high yields. Control experiments indicate the involvement of oxoammonium (TEMPO+) species in the coupling reaction outcomes.
A TEMPO-promoted method was developed for the synthesis of symmetric bis-N-Mannich bases via sequential activation of two alpha,alpha '-amino C(sp3)-H bonds of N,N-dimethylanilines under mild conditions. This methodology was further extended for monoimidation of alpha-amino-functionalized methylanilines to give unsymmetric N-Mannich bases in good to high yields. Several control experiments were performed, and the coupling reaction outcomes indicated that the oxoammonium (TEMPO+) species is involved in the reaction.
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