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Palladium‐Catalyzed Sequential Reactions via Allene Intermediates for the Rapid Synthesis of Fused Polycyclic Pyrrole Derivatives
Author(s) -
Huang Xian,
Zhu Shugao,
Shen Ruwei
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900503
Subject(s) - chemistry , sonogashira coupling , allene , isomerization , pyrrole , cycloaddition , propargyl , palladium , cascade reaction , combinatorial chemistry , catalysis , coupling reaction , photochemistry , triple bond , organic chemistry , double bond
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 CC bond and two CN bonds formed to construct the pyrrole unit, together with two rings efficiently assembled in one stroke.