A Catalytic Construction of Indoles via Formation of Ruthenium Vinylidene Species from  N ‐Arylynamides | Zendy

Tayu Masanori | Zendy; Watanabe Ryuta | Zendy; Isogi Satoshi | Zendy; Saito Nozomi | Zendy

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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.

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