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A Catalytic Construction of Indoles via Formation of Ruthenium Vinylidene Species from N ‐Arylynamides
Author(s) -
Tayu Masanori,
Watanabe Ryuta,
Isogi Satoshi,
Saito Nozomi
Publication year - 2021
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.202001342
Subject(s) - chemistry , ruthenium , indole test , catalysis , deuterium , molecule , combinatorial chemistry , cascade , functional group , stereochemistry , organic chemistry , quantum mechanics , physics , polymer , chromatography
Treatment of ynamides with a catalytic amount of TpRuCl(PPh 3 ) 2 resulted in the construction of indole scaffolds known as privileged structure motifs. This reaction involved a cascade of 1,2‐rearrangement and cyclization carrying out C−C bond formation via a ruthenium vinylidene intermediate, as revealed by a deuterium‐labeling experiments. Furthermore, the transformation of multi‐functionalized ynamide, derived from a practical drug molecule, showed a high functional group tolerance of this reaction.