期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 137, 期 35, 页码 11258-11261出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b07403
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资金
- NIH [GM071779]
- Direct For Mathematical & Physical Scien [1266405, 1402682] Funding Source: National Science Foundation
- Division Of Chemistry [1266405] Funding Source: National Science Foundation
- Division Of Materials Research [1402682] Funding Source: National Science Foundation
A PPh3-mediated multicomponent reaction between o-phthalaldehydes, nucleophiles, and monosubstituted allenes furnishes functionalized non-C-2-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 gamma-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.
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