Synthesis of 1,1′-diarylethanes and related systems by displacement of trichloroacetimidates with trimethylaluminum

Nivedita S. Mahajani, John D Chisholm

Research output: Contribution to journalArticle

3 Scopus citations

Abstract

Benzylic trichloroacetimidates are readily displaced by trimethylaluminum under Lewis acid promoted conditions to provide the corresponding methyl substitution product. This method is a convenient way to access 1,1′-diarylethanes and related systems, which play a significant role in medicinal chemistry, with a number of systems owing their biological activity to this functionality. Most benzylic substrates undergo ready displacement, with electron deficient systems being the exception. The use of an enantiopure imidate showed significant racemization, implicating the formation of a cationic intermediate.

Original languageEnglish (US)
Pages (from-to)4131-4139
Number of pages9
JournalJournal of Organic Chemistry
Volume83
Issue number7
DOIs
StatePublished - Apr 6 2018

    Fingerprint

ASJC Scopus subject areas

  • Organic Chemistry

Cite this