Rapid C-H Transformation: Addition of Diarylmethanes to Imines in Seconds by Catalytic Use of Base

Christian Weindl; Sebastian L Helmbrecht; Lukas Hintermann

doi:10.1021/acs.joc.2c02658

Rapid C-H Transformation: Addition of Diarylmethanes to Imines in Seconds by Catalytic Use of Base

J Org Chem. 2023 Apr 7;88(7):4155-4161. doi: 10.1021/acs.joc.2c02658. Epub 2023 Mar 27.

Authors

Christian Weindl^{1

2}, Sebastian L Helmbrecht^{1

2}, Lukas Hintermann^{1

2}

Affiliations

¹ Department Chemie, Technische Universität München, Lichtenbergstr. 4, 85748 Garching bei München, Germany.
² TUM Catalysis Research Center, Technische Universität München, Ernst-Otto-Fischer-Str. 1, 85748 Garching bei München, Germany.

PMID: 36972371
DOI: 10.1021/acs.joc.2c02658

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.