4.7 Article

Iridium-catalysed branched-selective hydroacylation of 1,3-dienes with salicylaldehydes

Journal

CHEMICAL COMMUNICATIONS
Volume 57, Issue 60, Pages 7378-7381

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d1cc01872h

Keywords

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Funding

  1. National Natural Science Foundation of China [21772043]
  2. Shanghai Pujiang Program [19PJ1403000]

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In this study, an iridium-catalyzed branched-selective hydroacylation of 1-aryl 1,3-dienes with salicylaldehydes was successfully conducted under mild conditions without the need for phosphine ligands. The protocol yielded a series of alpha-branched beta,gamma-unsaturated o-hydroxyacetophenones with biological potentials in high efficiency and excellent regioselectivities. Exclusive linear-selective hydroacylation products were obtained when simple 1,3-butadiene or isoprene were used instead of 1-aryl 1,3-dienes.
Herein, we report an iridium-catalyzed branched-selective hydroacylation of 1-aryl 1,3-dienes with salicylaldehydes under mild conditions with no need of phosphine ligands. With this protocol, a series of alpha-branched beta,gamma-unsaturated o-hydroxyacetophenones with biological potentials were synthesized in high efficiency with excellent regioselectivities. When simple 1,3-butadiene or isoprene instead of 1-aryl 1,3-dienes were used, exclusive linear-selective hydroacylation products were obtained.

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