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Palladium‐Catalyzed C–C Ring Closure in α‐Chloromethylimines: Synthesis of 1 H ‐Indoles
Author(s) -
Bellezza Delia,
Noverges Bárbara,
Fasano Francesco,
Sarmiento Jeymy T.,
MedioSimón Mercedes,
Asensio Gregorio
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801607
Subject(s) - chemistry , aryl , ring (chemistry) , palladium , alkyl , medicinal chemistry , benzene , catalysis , amine gas treating , organic chemistry
The C‐C ring closure of α‐chloromethyl alkyl or aryl N‐aryl imines catalyzed with 1 to 10 % Pd(OAc) 2 /P(p‐tolyl) 3 afford efficiently 2‐aryl‐ and 2‐alkyl‐1 H‐ indoles. The heterocyclization reaction involves the initial formation of [2‐(arylimino)ethyl]palladium(II) chloride complexes with subsequent C‐H activation of the aromatic amine ring. Readily or commercially available α‐chloromethyl‐aryl or ‐alkyl ketones are used as the precursors. Functionalized indoles at the benzene ring are obtained when the imines are derived from substituted anilines.