ChemInform Abstract: Gold‐Catalyzed Carbocyclization of Phenols with a Terminal Alkyne via an Intramolecular ipso‐Friedel—Crafts Alkenylation.

Abstract

A new method to synthesize spiro[4.5]cyclohexadienone derivatives with an exo‐cyclic olefin unit is developed.

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

“… 355 Spiro[4.5]cyclohexadienones have been also obtained by a gold(I)-catalyzed carbocyclization of phenols with a terminal alkyne via intramolecular ipso -Friedel–Crafts. 356 Aryl alkynylphosphonates also undergo intramolecular gold(I)-catalyzed hydroarylation to give phosphacoumarins. 357 …”

“…Aryl alkynoate esters 407 afford coumarin derivatives 408 in the presence of gold­(I) by intramolecular hydroarylation under anhydrous conditions (Scheme ). ,, It has been recently reported that the same substrates under the same reaction conditions swapping from anhydrous to wet solvent undergo a gold­(I)-catalyzed spirocyclization under mild conditions, giving spirolactones 409 in high yields . Spiro[4.5]­cyclohexadienones have been also obtained by a gold­(I)-catalyzed carbocyclization of phenols with a terminal alkyne via intramolecular ipso -Friedel–Crafts . Aryl alkynylphosphonates also undergo intramolecular gold­(I)-catalyzed hydroarylation to give phosphacoumarins …”