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Au I Iminophosphorane Complexes as Efficient Catalysts for the Cycloisomerization of Alkynyl Amides under Air, at Room Temperature, and in Aqueous or Eutectic‐Mixture Solutions
Author(s) -
RodríguezÁlvarez María J.,
Vidal Cristian,
Schumacher Sören,
Borge Javier,
GarcíaÁlvarez Joaquín
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201605303
Subject(s) - cycloisomerization , catalysis , chemistry , eutectic system , phosphine , aqueous solution , choline chloride , chloride , salt (chemistry) , medicinal chemistry , cyclopentane , organic chemistry , alloy
New iminophosphorane‐phosphine Au I complexes [AuCl(κ 1 ‐ P ‐Ph 2 PCH 2 P{=NP(=S)(OR) 2 }Ph 2 )] ( 3 a , b ) and [Au 2 Cl 2 (μ 2 ‐ P , S ‐Ph 2 PCH 2 P{=NP(=S)(OR) 2 }Ph 2 )] ( 4 a , b ) proved to be general, very efficient, and recyclable (up to four consecutive runs) catalysts for the cycloisomerization of alkynyl amides in water or choline chloride‐based eutectic mixtures as green solvents. Remarkably, this cycloisomerization reaction took place under mild conditions (low catalyst loading, at room temperature, and in the absence of cocatalysts or protecting atmosphere) to give the corresponding alkylidene lactams by employing an efficient and sustainable methodology.