Rapid C-H Transformation: Addition of Diarylmethanes to Imines in Seconds by Catalytic Use of Base.
J Org Chem
; 88(7): 4155-4161, 2023 Apr 07.
Article
em En
| MEDLINE
| ID: mdl-36972371
ABSTRACT
The addition of diarylmethanes or methylarenes via activation of benzylic C(sp3)-H bonds to N-aryl imines proceeds under catalysis by alkali hexamethyldisilazide (HMDS) base to give N-(1,2,2-triarylethyl)anilines or N-(1,2-diarylethyl)anilines, respectively. In the presence of 10 mol % of LiHMDS at room temperature, the diarylmethane addition equilibrates within 20-30 s and is driven to near completion by cooling the reaction mixture to -25 °C, providing N-(1,2,2-triarylethyl)aniline in a >90% yield.
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MEDLINE
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En
Ano de publicação:
2023
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Article