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Bicyclization of Isocyanides: A Synthetic Strategy for Fused Pyrroles
Author(s) -
Zhang Lingjuan,
Xu Xianxiu,
Xia Wenming,
Liu Qun
Publication year - 2011
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.201100501
Subject(s) - chemistry , electrophile , isocyanide , carbon atom , combinatorial chemistry , sigma bond , carbon fibers , organic chemistry , molecule , catalysis , ring (chemistry) , materials science , composite number , composite material
On the isocyanide carbon atom, two CC sigma bonds are formed in the bicyclization reaction of the readily available acyclic substrates with tosylmethyl isocyanides. The reaction can proceed under extremely mild and metal‐free conditions to give the products in high to excellent yields. The powerful potential of this strategy deserves attention because it is a new paradigm for trapping of the incipient imidoyl anion, by a carbon electrophile instead of a proton.