title: Rh(III)-Catalyzed [4 + 1] Annulations of 2-Hydroxy- and 2-Aminobenzaldehydes with Allenes: A Simple Method toward 3-Coumaranones and 3-Indolinones.
abstract: A novel method for the regio- and stereoselective synthesis of substituted 3-coumaranones from salicylaldehydes and allenes using a rhodium(III) catalyst has been developed. This procedure gives access to new 2-vinyl-substituted 3-coumaranone compounds. The method involves a Rh(III)-catalyzed aldehyde C-H activation and annulation reactions. Moreover, this Rh(III)-catalyzed [4 + 1] annulation reaction has been applied to 2-aminobenzaldehydes to afford 2,2-disubstituted 3-indolinones.
authors.affiliation: Department of Chemistry, National Tsing Hua University, Hsinchu 30013, Taiwan.
authors.forename: Ramajayam
authors.initials: R
authors.lastname: Kuppusamy
authors.affiliation: Department of Chemistry, National Tsing Hua University, Hsinchu 30013, Taiwan.
authors.forename: Parthasarathy
authors.initials: P
authors.lastname: Gandeepan
authors.affiliation: Department of Chemistry, National Tsing Hua University, Hsinchu 30013, Taiwan.
authors.forename: Chien-Hong
authors.initials: CH
authors.lastname: Cheng
mesh_terms: D000466:Alkadienes / Q000737:chemistry*; D001547:Benzaldehydes / Q000737:chemistry*; D002384:Catalysis; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C585771:3-coumaranone; D000466:Alkadienes; D001547:Benzaldehydes; D003374:Coumarins; D007211:Indoles; C025947:propadiene; C000062:2-aminobenzaldehyde; D012238:Rhodium