title: Phosphine-Mediated Iterative Arene Homologation Using Allenes.
abstract: A PPh3-mediated multicomponent reaction between o-phthalaldehydes, nucleophiles, and monosubstituted allenes furnishes functionalized non-C2-symmetric naphthalenes in synthetically useful yields. When the o-phthalaldehydes were reacted with 1,3-disubstituted allenes in the presence of PPh2Et, naphthalene derivatives were also obtained in up to quantitative yields. The mechanism of the latter transformation is straightforward: aldol addition followed by Wittig olefination and dehydration. The mechanism of the former is a tandem γ-umpolung/aldol/Wittig/dehydration process, as established by preparation of putative reaction intermediates and mass spectrometric analysis. This transformation can be applied iteratively to prepare anthracenes and tetracenes using carboxylic acids as pronucleophiles.
authors: Department of Chemistry and Biochemistry, University of California , Los Angeles, California 90095-1569, United States.
authors: Kui
authors: K
authors: Zhang
authors: Department of Chemistry and Biochemistry, University of California , Los Angeles, California 90095-1569, United States.
authors: Lingchao
authors: L
authors: Cai
authors: Department of Chemistry and Biochemistry, University of California , Los Angeles, California 90095-1569, United States.
authors: Xing
authors: X
authors: Jiang
authors: Department of Chemistry and Biochemistry, University of California , Los Angeles, California 90095-1569, United States.
authors: Miguel A
authors: MA
authors: Garcia-Garibay
authors: Department of Chemistry and Biochemistry, University of California , Los Angeles, California 90095-1569, United States.
authors: Ohyun
authors: O
authors: Kwon
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D009281:Naphthalenes / Q000737:chemistry; D010720:Phosphines / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D000475:Alkenes; D006841:Hydrocarbons, Aromatic; D009281:Naphthalenes; D010720:Phosphines; C031721:naphthalene; C044646:phosphine