Gold(I)-catalyzed benzannulation of 3-hydroxy-1,5-enynes: an efficient synthesis of substituted tetrahydronaphthalenes and related compounds

Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity

“…Boc-protected 3-hydroxy-1,5-enynes form cyclohex-4-ene-1,2-diol derivatives 214 . 220 Gold(I) complexes also catalyze formation of benzene derivatives 215 from 3-hydroxy-1,5-enynes, 221 which can also be generated in situ by the addition of allylsilanes to alkynals. 222 …”

Synthesis and Study of Cationic, Two‐Coordinate Triphenylphosphine– Gold–π Complexes

“…[17] Although monomeric triphenylphosphine-gold-p complexes have escaped isolation, a number of these complexes have been purportedly generated in situ from reaction of a p ligand with either a mixture of [(PPh 3 )AuCl] and silver salt or with a single-component gold complex, such as [(PPh 3 )AuNTf 2 ]. [18][19][20][21][22][23] However, there are a number of inconsistencies in the reported spectroscopy and solution behavior of these complexes that warrant further investigation. In most cases, characterization of the purported triphenylphosphine-gold-p complex rests solely on 31 P NMR analysis recorded at or above room temperature with reported chemical shifts ranging from d = 28 to 45 ppm.…”

Coinage-Metal-Catalyzed Reactions of Propargylic Alcohols

“…Using gold(I) and silver(I) catalysts, Barriault and coworkers reported a novel benzannulation method to produce diverse functionalized tetrahydronaphthalene compounds 178 from 3-hydroxy-1,5-enyne substrates 177 (Scheme 79). 94,95 The high catalytic proficiency was demonstrated using a Au(PPh 3 )Cl/TfOH catalyst system. 95 This study was the first to report an active gold catalytic system consisting of Au(PPh 3 )Cl and triflic acid.…”

“…94,95 The high catalytic proficiency was demonstrated using a Au(PPh 3 )Cl/TfOH catalyst system. 95 This study was the first to report an active gold catalytic system consisting of Au(PPh 3 )Cl and triflic acid. Recently, Li and Liu revealed an efficient and rapid synthesis of polysubstituted 1-naphthols 180 through the gold-catalyzed endo-furan-yne cyclization of 1-(2-furanyl)phenyl propargylic alcohols 179 involving a 1,2-rearrangement (Scheme 80).…”