4.7 Article

Palladium-Catalyzed Sequential Reactions via Allene Intermediates for the Rapid Synthesis of Fused Polycyclic Pyrrole Derivatives

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 351, Issue 18, Pages 3118-3122

Publisher

WILEY-BLACKWELL
DOI: 10.1002/adsc.200900503

Keywords

allenes; palladium-catalyzed reactions; pyrroles; sequential reactions

Funding

  1. National Natural Science Foundation of China [20732005, 20872127]
  2. National Basic Research Program of China [2009CB825300]

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In this paper, we report a novel sequential reaction sequence consisting of a series of processes including Sonogashira coupling, propargyl-allenyl isomerization, [3+2]cycloaddition, denitrogenation, and highly selective biradical coupling reaction, providing an efficient synthesis of fused polycyclic pyrrole derivatives. The reaction features one C-C bond and two C-N bonds formed to construct the pyrrole unit, together with two rings efficiently assembled in one stroke.

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