title: Divergent Reactivity of Rhodium(I) Carbenes Derived from Indole Annulations.
abstract: Rhodium(I) carbenes were generated from propargylic alcohol derivatives as the result of a dehydrative indole annulation. Depending on the choice of the electron-withdrawing group on the aniline nitrogen nucleophile, either a cyclopropanation product or dimerization product was obtained chemoselectively. Intramolecular hydroamidation occurred for the same type of propargylic alcohol derivatives when other transition-metal catalysts were employed.
authors.affiliation: School of Pharmacy, University of Wisconsin-Madison, Madison, WI 53705-2222 (USA).
authors.forename: Xiaoxun
authors.initials: X
authors.lastname: Li
authors.affiliation: School of Pharmacy, University of Wisconsin-Madison, Madison, WI 53705-2222 (USA).
authors.forename: Hui
authors.initials: H
authors.lastname: Li
authors.affiliation: School of Pharmacy, University of Wisconsin-Madison, Madison, WI 53705-2222 (USA).
authors.forename: Wangze
authors.initials: W
authors.lastname: Song
authors.affiliation: School of Pharmacy, University of Wisconsin-Madison, Madison, WI 53705-2222 (USA).
authors.forename: Po-Sen
authors.initials: PS
authors.lastname: Tseng
authors.affiliation: School of Pharmacy, University of Wisconsin-Madison, Madison, WI 53705-2222 (USA). liulingyan@nankai.edu.cn.|Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071 (P.R. China). liulingyan@nankai.edu.cn.
authors.forename: Lingyan
authors.initials: L
authors.lastname: Liu
authors.affiliation: Department of Chemistry, University of Wisconsin-Madison, Madison, WI 53706 (USA).
authors.forename: Ilia A
authors.initials: IA
authors.lastname: Guzei
authors.affiliation: School of Pharmacy, University of Wisconsin-Madison, Madison, WI 53705-2222 (USA). wtang@pharmacy.wisc.edu.|Department of Chemistry, University of Wisconsin-Madison, Madison, WI 53706 (USA). wtang@pharmacy.wisc.edu.
authors.forename: Weiping
authors.initials: W
authors.lastname: Tang
mesh_terms: D007211:Indoles / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*
chemical_list: D007211:Indoles; D009942:Organometallic Compounds; C030011:carbene; D012238:Rhodium; D008697:Methane
keywords: carbenes; cyclizations; heterocycles; rhodium; synthetic methods