Graphene-Catalyzed Direct Friedel-Crafts Alkylation Reactions: Mechanism, Selectivity, and Synthetic Utility

Feng Hu, Mehulkumar Patel, Feixiang Luo, Carol Flach, Richard Mendelsohn, Eric Garfunkel, Huixin He, Michal Szostak

Research output: Contribution to journalArticle

71 Citations (Scopus)

Abstract

Transition-metal-catalyzed alkylation reactions of arenes have become a central transformation in organic synthesis. Herein, we report the first general strategy for alkylation of arenes with styrenes and alcohols catalyzed by carbon-based materials, exploiting the unique property of graphenes to produce valuable diarylalkane products in high yields and excellent regioselectivity. The protocol is characterized by a wide substrate scope and excellent functional group tolerance. Notably, this process constitutes the first general application of graphenes to promote direct C-C bond formation utilizing polar functional groups anchored on the GO surface, thus opening the door for an array of functional group alkylations using benign and readily available graphene materials. Mechanistic studies suggest that the reaction proceeds via a tandem catalysis mechanism in which both of the coupling partners are activated by interaction with the GO surface.

Original languageEnglish
Pages (from-to)14473-14480
Number of pages8
JournalJournal of the American Chemical Society
Volume137
Issue number45
DOIs
Publication statusPublished - Oct 23 2015

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Alkylation
Graphene
Functional groups
Styrenes
Synthetic Chemistry Techniques
Regioselectivity
Catalysis
Transition metals
Styrene
Alcohols
Carbon
Metals
Substrates

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Graphene-Catalyzed Direct Friedel-Crafts Alkylation Reactions : Mechanism, Selectivity, and Synthetic Utility. / Hu, Feng; Patel, Mehulkumar; Luo, Feixiang; Flach, Carol; Mendelsohn, Richard; Garfunkel, Eric; He, Huixin; Szostak, Michal.

In: Journal of the American Chemical Society, Vol. 137, No. 45, 23.10.2015, p. 14473-14480.

Research output: Contribution to journalArticle

Hu, Feng ; Patel, Mehulkumar ; Luo, Feixiang ; Flach, Carol ; Mendelsohn, Richard ; Garfunkel, Eric ; He, Huixin ; Szostak, Michal. / Graphene-Catalyzed Direct Friedel-Crafts Alkylation Reactions : Mechanism, Selectivity, and Synthetic Utility. In: Journal of the American Chemical Society. 2015 ; Vol. 137, No. 45. pp. 14473-14480.
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