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1,6‐Enyne Cyclizations Catalyzed by N‐Heterocyclic Carbene Supported Gold Complexes: Deconvoluting Sterics and Electronics
Author(s) -
Arumugam Kuppuswamy,
Varghese Bibin,
Brantley Johnathan N.,
Konda Sai S. M.,
Lynch Vincent M.,
Bielawski Christopher W.
Publication year - 2014
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.201301137
Subject(s) - enyne , chemistry , cycloisomerization , carbene , catalysis , steric effects , bicyclic molecule , selectivity , electronic effect , enyne metathesis , organic chemistry , combinatorial chemistry , medicinal chemistry , metathesis , polymer , polymerization
A series of N‐heterocyclic carbene (NHC) supported gold(I) complexes were synthesized, characterized in solution as well as in the solid state, and examined as precatalysts for 1,6‐enyne cycloisomerization reactions. The product mixtures obtained for a variety of 1,6‐enyne isomerizations were governed primarily by the electronic properties of the aforementioned precatalysts. In particular, precatalysts containing electronic‐rich NHC ligands showed increased selectivity for bicyclic products, whereas analogous precatalysts supported by electron‐deficient NHCs preferentially afforded olefinic products.