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Domino C−S/C−N Bond Formation Using Well‐Defined Copper‐Phosphine Complex Catalyst: Divergent Approach to 3‐Sulfenylated Indoles
Author(s) -
Tamargo Ramuel John Inductivo,
Kim Sung Hong,
Lee Yong Rok
Publication year - 2019
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.201900612
Subject(s) - domino , chemistry , chemoselectivity , intramolecular force , phosphine , catalysis , combinatorial chemistry , copper , substrate (aquarium) , cascade reaction , organic chemistry , oceanography , geology
A protocol was developed for the synthesis of 3‐thioindoles in good‐to‐excellent yields involving sulfenylation between 2‐nitrocinnamaldehydes and various thiols using a well‐defined copper(I)‐phosphine complex catalyst. This unconventional divergent approach involves in situ generation of indoles via domino C−S/C−N bond formation initiated by sulfa‐Michael addition followed by intramolecular N ‐heteroannulation. This protocol shows good chemoselectivity and broad substrate scope. To briefly demonstrate the value of this approach, 2‐benzoyl‐3‐sulfenylated indoles were prepared from commercially available 2‐nitrochalcones and thiols.