Controllable, sequential, and stereoselective C–H allylic alkylation of alkenes

Ling Qin, Mohammed Sharique, Uttam K. Tambar

Research output: Contribution to journalArticlepeer-review

Abstract

The direct conversion of C–H bonds into new C–C bonds represents a powerful approach to generate complex molecules from simple starting materials. However, a general and controllable method for the sequential conversion of a methyl group into a fully substituted carbon center remains a challenge. We report a new method for the selective and sequential replacement of three C-H bonds at the allylic position of propylene and other simple terminal alkenes with different carbon groups derived from Grignard reagents. A copper catalyst and electron-rich biaryl phosphine ligand facilitate the formation of allylic alkylation products in high branch-selectivity. We also present conditions for the generation of enantioenriched allylic alkylation products in the presence of catalytic copper and a chiral phosphine ligand. With this approach, diverse and complex products with substituted carbon centers can be generated from simple and abundant feedstock chemicals.

Original languageEnglish (US)
JournalUnknown Journal
DOIs
StatePublished - Aug 17 2019

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)
  • Materials Science(all)

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