ChemInform Abstract: Reaction of 2-Hydroxybenzaldehydes with Alkynes, Alkenes, or Allenes via Cleavage of the Aldehyde C—H Bond Using a Rhodium Catalyst System.

✍ Scribed by Ken Kokubo; Kenji Matsumasa; Yuko Nishinaka; Masahiro Miura; Masakatsu Nomura

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 34 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199923109

✦ Synopsis

Reaction of 2-Hydroxybenzaldehydes with Alkynes, Alkenes, or Allenes via Cleavage of the Aldehyde C-H Bond Using a Rhodium Catalyst System. -Aldehyde (I) smoothly reacts with internal and terminal alkynes to give alkenoylphenols in good to excellent yields. The substituents of acetylene influence the regioselectivity. For example, an oxygen function on the propargylic position, cf. (IVc) and (IVd), yields good regioselectivities. Furthermore, in place of alkynes some alkenes or allenes, e.g. (X) and (XIII), react also with hydroxybenzaldehydes, although 1,3-dienes such as isoprene and myrcene cannot be used. -(KOKUBO, KEN; MATSUMASA, KENJI;