Ligand-controlled access to [4 + 2] and [4 + 3] cycloadditions in gold-catalyzed reactions of allene-dienes.
By adjustment of the electronic properties of the ancilliary ligands, high selectivity can be achieved for either [4 + 2] or [4 + 3] cycloaddition reactions of allene-dienes catalyzed by gold(I). Triarylphosphitegold(I) complexes are employed as catalysts for a [4 + 2] cycloaddition reaction leading to alkylidenecyclohexenes. Conversely, di-tert-butylbiphenylphosphinegold(I)-catalyzed reactions afford cycloheptadienes via [4 + 3] cycloaddition reactions.
Mauleón
Pablo
P
Department of Chemistry, University of California, Berkeley, California 94720, USA.
Zeldin
Rachel M
RM
González
Ana Z
AZ
Toste
F Dean
FD
D000466:Alkadienes / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D055598:Chemical Phenomena; D003508:Cycloheptanes / Q000138:chemical synthesis*; D053138:Cyclohexenes / Q000138:chemical synthesis*; D006046:Gold / Q000737:chemistry*; D008024:Ligands
D000466:Alkadienes; D000475:Alkenes; D003508:Cycloheptanes; D053138:Cyclohexenes; D008024:Ligands; D006046:Gold