Ruthenium-Catalyzed Monoalkenylation of Aromatic Ketones by Cleavage of Carbon-Heteroatom Bonds with Unconventional Chemoselectivity

Hikaru Kondo, Nana Akiba, Takuya Kochi, Fumitoshi Kakiuchi

研究成果: Article

25 引用 (Scopus)

抄録

Ruthenium-catalyzed selective monoalkenylation of ortho C-O or C-N bonds of aromatic ketones was achieved. The reaction allowed the direct comparison of the relative reactivities of the cleavage of different carbon-heteroatom bonds, thus suggesting an unconventional chemoselectivity, where smaller, more-electron-donating groups are more easily cleaved. Selective monofunctionalization of C-O bonds in the presence of ortho C-H bonds was also achieved. Smaller is better: The title reaction for ortho C-O and C-N bonds of aromatic ketones was achieved. Direct comparison of the cleavage of the carbon-heteroatom bonds suggested an unconventional chemoselectivity, where smaller, more-electron-donating groups are more easily cleaved. Selective monofunctionalization of C-O bonds in the presence of ortho C-H bonds was also achieved.

元の言語English
ページ(範囲)9293-9297
ページ数5
ジャーナルAngewandte Chemie - International Edition
54
発行部数32
DOI
出版物ステータスPublished - 2015 8 1

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Ruthenium
Ketones
Carbon
Electrons

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

これを引用

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AU - Kondo, Hikaru

AU - Akiba, Nana

AU - Kochi, Takuya

AU - Kakiuchi, Fumitoshi

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N2 - Ruthenium-catalyzed selective monoalkenylation of ortho C-O or C-N bonds of aromatic ketones was achieved. The reaction allowed the direct comparison of the relative reactivities of the cleavage of different carbon-heteroatom bonds, thus suggesting an unconventional chemoselectivity, where smaller, more-electron-donating groups are more easily cleaved. Selective monofunctionalization of C-O bonds in the presence of ortho C-H bonds was also achieved. Smaller is better: The title reaction for ortho C-O and C-N bonds of aromatic ketones was achieved. Direct comparison of the cleavage of the carbon-heteroatom bonds suggested an unconventional chemoselectivity, where smaller, more-electron-donating groups are more easily cleaved. Selective monofunctionalization of C-O bonds in the presence of ortho C-H bonds was also achieved.

AB - Ruthenium-catalyzed selective monoalkenylation of ortho C-O or C-N bonds of aromatic ketones was achieved. The reaction allowed the direct comparison of the relative reactivities of the cleavage of different carbon-heteroatom bonds, thus suggesting an unconventional chemoselectivity, where smaller, more-electron-donating groups are more easily cleaved. Selective monofunctionalization of C-O bonds in the presence of ortho C-H bonds was also achieved. Smaller is better: The title reaction for ortho C-O and C-N bonds of aromatic ketones was achieved. Direct comparison of the cleavage of the carbon-heteroatom bonds suggested an unconventional chemoselectivity, where smaller, more-electron-donating groups are more easily cleaved. Selective monofunctionalization of C-O bonds in the presence of ortho C-H bonds was also achieved.

KW - boron

KW - chemoselectivity

KW - ruthenium

KW - substituent effects

KW - synthetic methods

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