4.6 Article

A Simple Catalyst for the Efficient Benzylation of Arenes by Using Alcohols, Ethers, Styrenes, Aldehydes, or Ketones

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 15, Issue 18, Pages 4610-4613

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200802740

Keywords

arenes; benzylation; hydroarylation; hydrogen transfer; N-heterocyclic carbenes; tandem reactions

Funding

  1. Ministerio de Ciencia e Innovacion [CTQ2008-04460]
  2. Bancaixa [P1.1B2007-04]
  3. Spanish Ministerio de Ciencia e Innovacion
  4. Juan de la Cierva program

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The compound [IrCp*(OTf)(2)(I-nBu)] (I-nBu = 1,3-di-n-butyl-imidazolylidene) is an effective catalyst in the benzylation of arenes with different benzylating agents, such as alcohols, ethers and styrenes, representing ail unprecedented highly versatile catalyst for this type of process. The same compound also catalyses a remarkable tandem process that allows the use of aldehydes and ketones as benzylating agents, through the base-free hydrogenation of C=O bonds with iPrOH and further use of the resulting primary or secondary alcohols as benzylating agents.

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