Journal
ORGANIC LETTERS
Volume 23, Issue 5, Pages 1594-1599Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c04306
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Funding
- American Chemical Society [59570-ND1]
- US NSF [CHE-1902509]
- National Natural Science Foundation of China [21772001, 21801128, 22071107]
- Cultivation Project for University Outstanding Talents of Anhui Province
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A novel method for synthesizing 2-azaaryl tetrahydroquinolines is reported by the base-promoted tandem reaction of azaaryl methyl amines and styrene derivatives. Mechanistic probe experiments confirm the mechanism involving deprotonation of the benzylic C-H bond and addition to the styrene vinyl group via the SNAr mechanism. High yields of up to 95% were achieved in over 30 examples, demonstrating the potential applicability of this method.
A novel method to synthesize 2-azaaryl tetrahydroquinolines by the base-promoted tandem reaction of azaaryl methyl amines and styrene derivatives is reported (over 30 examples, yields up to 95%). Mechanistic probe experiments demonstrate that the deprotonation of the benzylic C-H bond and the addition to the styrene vinyl group proceeds via the SNAr mechanism.
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