About: Chemoselective Synthesis of 4,5-Diarylpyrrolo[2,3-d]pyrimidines (6,7-Diaryl-7-deazapurines) by Consecutive Suzuki and Liebeskind-Srogl Cross-Couplings     Goto   Sponge   NotDistinct   Permalink

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Description
  • A new chemoselective synthesis of pyrrolo[2,3-d]pyrimidines (7-deazapurines) bearing two different aryl groups at positions 4 and 5 was developed based on two orthogonal cross-couplings. Starting from 7-benzyl-protected 4-(phenylsulfanyl)-5-iodopyrrolo[2,3-d] pyrimidine, the Pd-catalyzed Suzuki coupling with arylboronic acids proceeded selectively at position 5, followed by the Pd-catalyzed Cu-mediated Liebeskind-Srogl coupling at position 4. A small library of 4,5-diaryl derivatives was prepared.
  • A new chemoselective synthesis of pyrrolo[2,3-d]pyrimidines (7-deazapurines) bearing two different aryl groups at positions 4 and 5 was developed based on two orthogonal cross-couplings. Starting from 7-benzyl-protected 4-(phenylsulfanyl)-5-iodopyrrolo[2,3-d] pyrimidine, the Pd-catalyzed Suzuki coupling with arylboronic acids proceeded selectively at position 5, followed by the Pd-catalyzed Cu-mediated Liebeskind-Srogl coupling at position 4. A small library of 4,5-diaryl derivatives was prepared. (en)
Title
  • Chemoselective Synthesis of 4,5-Diarylpyrrolo[2,3-d]pyrimidines (6,7-Diaryl-7-deazapurines) by Consecutive Suzuki and Liebeskind-Srogl Cross-Couplings
  • Chemoselective Synthesis of 4,5-Diarylpyrrolo[2,3-d]pyrimidines (6,7-Diaryl-7-deazapurines) by Consecutive Suzuki and Liebeskind-Srogl Cross-Couplings (en)
skos:prefLabel
  • Chemoselective Synthesis of 4,5-Diarylpyrrolo[2,3-d]pyrimidines (6,7-Diaryl-7-deazapurines) by Consecutive Suzuki and Liebeskind-Srogl Cross-Couplings
  • Chemoselective Synthesis of 4,5-Diarylpyrrolo[2,3-d]pyrimidines (6,7-Diaryl-7-deazapurines) by Consecutive Suzuki and Liebeskind-Srogl Cross-Couplings (en)
skos:notation
  • RIV/00216208:11310/14:10283182!RIV15-MSM-11310___
http://linked.open...avai/riv/aktivita
http://linked.open...avai/riv/aktivity
  • I, P(GAP207/12/0205)
http://linked.open...iv/cisloPeriodika
  • 32
http://linked.open...vai/riv/dodaniDat
http://linked.open...aciTvurceVysledku
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  • 7118
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  • RIV/00216208:11310/14:10283182
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  • nitrogen heterocycles; palladium; cross-coupling; chemoselectivity; synthetic methods (en)
http://linked.open.../riv/klicoveSlovo
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  • DE - Spolková republika Německo
http://linked.open...ontrolniKodProRIV
  • [EC1296E6197F]
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  • European Journal of Organic Chemistry
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  • neuveden
http://linked.open...iv/tvurceVysledku
  • Hocek, Michal
  • Klepetářová, Blanka
  • Slavětínská, Lenka
  • Klečka, Martin
  • Krömer, Matouš
http://linked.open...ain/vavai/riv/wos
  • 000344624000017
issn
  • 1434-193X
number of pages
http://bibframe.org/vocab/doi
  • 10.1002/ejoc.201402882
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  • 11310
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