title: Rhodium-catalyzed direct annulation of aldehydes with alkynes leading to indenones: proceeding through in situ directing group formation and removal.
abstract: The Rh-catalyzed direct annulation of an aldehyde with an alkyne leading to indenone was achieved. The in situ temporal installation of acetylhydrazine enables the annulation of the ortho arene C-H bond with alkynes to form ketone hydrazone. Subsequently, the in situ directing group removal takes place since ketone hydrazone is more susceptible toward hydrolysis than aldehyde hydrazone. Notably, this procedure tolerates a series of functional groups, such as methoxyl, acetylamino, fluoro, trifluoromethyl, methoxycarbonyl, chloro, and bromo groups.
authors.affiliation: School of Petrochemical Engineering, Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, Changzhou University , Changzhou 213164, P. R. China, and College of Chemistry & Engineering, Wenzhou University , Wenzhou, 325000, P. R. China.
authors.forename: Shuyou
authors.initials: S
authors.lastname: Chen
authors.forename: Jintao
authors.initials: J
authors.lastname: Yu
authors.forename: Yan
authors.initials: Y
authors.lastname: Jiang
authors.forename: Fan
authors.initials: F
authors.lastname: Chen
authors.forename: Jiang
authors.initials: J
authors.lastname: Cheng
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D001547:Benzaldehydes / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D007189:Indans / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000480:Alkynes; D001547:Benzaldehydes; D007189:Indans; D007659:Ketones; D012238:Rhodium; C032175:benzaldehyde