I2‑Catalyzed Aerobic α,β-Dehydrogenation
and Deamination of Tertiary Alkylamines: Highly Selective Synthesis
of Polysubstituted Pyrimidines via Hidden Acyclic Enamines
Posted on 2020-07-07 - 19:43
A novel and efficient
entrance to the pyrimidine skeleton has been
presented via the α,β-dehydrogenation and deamination
of tertiary alkylamines. This I2-catalyzed dehydrogenative
multicomponent procedure utilizes simple aldehydes to trap the hidden
enamine intermediates and suspend generation of azadienes from amidines,
enabling the difunctionalization of a vicinal C(sp3)–H
bond. These studies provide valuable possibilities for the introduction
of aliphatic substituents and show how to switch to a new reactive
modality.
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Gao, Qinghe; Wu, Manman; Zhang, Ke; Yang, Ning; Liu, Mengting; Li, Juan; et al. (2020). I2‑Catalyzed Aerobic α,β-Dehydrogenation
and Deamination of Tertiary Alkylamines: Highly Selective Synthesis
of Polysubstituted Pyrimidines via Hidden Acyclic Enamines. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.0c02001
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AUTHORS (9)
QG
Qinghe Gao
MW
Manman Wu
KZ
Ke Zhang
NY
Ning Yang
ML
Mengting Liu
JL
Juan Li
LF
Lizhen Fang
SB
Suping Bai
YX
Yongtao Xu
KEYWORDS
Aerobicpyrimidine skeletondehydrogenationdehydrogenative multicomponent proc...Polysubstituted Pyrimidinesintroductionenamine intermediatesgenerationaldehydeDeaminationreactive modalityTertiary Alkylaminestrapdeaminationaliphatic substituentsamidinealkylamineCatalyzeddifunctionalizationAcyclic EnaminesDehydrogenationvicinalazadieneSelective Synthesisbond