Graphene oxide catalyzed ketone α-alkylation with alkenes: Enhancement of graphene oxide activity by hydrogen bonding

Guangrong Meng, Mehulkumar Patel, Feixiang Luo, Qingdong Li, Carol Flach, Richard Mendelsohn, Eric Garfunkel, Huixin He, Michal Szostak

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Direct α-alkylation of carbonyl compounds represents a fundamental bond forming transformation in organic synthesis. We report the first ketone-alkylation using olefins and alcohols as simple alkylating agents catalyzed by graphene oxide. Extensive studies of the graphene surface suggest a pathway involving dual activation of both coupling partners. Notably, we show that polar functional groups have a stabilizing effect on the GO surface, which results in a net enhancement of the catalytic activity. The method represents the first alkylation of carbonyl compounds using graphenes, which opens the door for the development of an array of protocols for ketone functionalization employing common carbonyl building blocks and readily available graphenes.

Original languageEnglish
Pages (from-to)5379-5382
Number of pages4
JournalChemical Communications
Volume55
Issue number37
DOIs
Publication statusPublished - Jan 1 2019

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Graphite
Alkylation
Alkenes
Ketones
Oxides
Graphene
Olefins
Carbonyl compounds
Hydrogen bonds
Thermodynamic properties
Alkylating Agents
Functional groups
Catalyst activity
Alcohols
Chemical activation

ASJC Scopus subject areas

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

Cite this

Graphene oxide catalyzed ketone α-alkylation with alkenes : Enhancement of graphene oxide activity by hydrogen bonding. / Meng, Guangrong; Patel, Mehulkumar; Luo, Feixiang; Li, Qingdong; Flach, Carol; Mendelsohn, Richard; Garfunkel, Eric; He, Huixin; Szostak, Michal.

In: Chemical Communications, Vol. 55, No. 37, 01.01.2019, p. 5379-5382.

Research output: Contribution to journalArticle

Meng, Guangrong ; Patel, Mehulkumar ; Luo, Feixiang ; Li, Qingdong ; Flach, Carol ; Mendelsohn, Richard ; Garfunkel, Eric ; He, Huixin ; Szostak, Michal. / Graphene oxide catalyzed ketone α-alkylation with alkenes : Enhancement of graphene oxide activity by hydrogen bonding. In: Chemical Communications. 2019 ; Vol. 55, No. 37. pp. 5379-5382.
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