Gold-catalyzed oxidative cycloalkenations of alkynes with quinoline N-oxides. Issue 2 (14th December 2018)

• Record Type: Journal Article
• Authors: Wagh, Sachin Bhausaheb; Sharma, Pankaj; Patil, Manoj D.; Liu, Rai-Shung
• Is Part Of: Organic chemistry frontiers. Volume 6:Issue 2(2019)
• Page Start: 226
• Page End: 230
• Publication Date: 2018-12-14
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c8qo01175c
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : This work reports gold-catalyzed oxidative cycloalkenations of phenyl propargyl ethers and phenoxyalkynes with quinoline N -oxides to afford 4-alkylidenechroman-2-ones and 3-alkylidenebenzofuran-2-ones respectively. Abstract : This work reports gold-catalyzed oxidative cycloalkenations of phenyl propargyl ethers and phenoxyalkynes with quinoline N -oxides to afford 4-alkylidenechroman-2-ones and 3-alkylidenebenzofuran-2-ones, respectively. This catalytic sequence involves one alkyne, one aryl nucleophile and two discrete quinoline oxides. We postulate a mechanism involving an initial formation of an α-oxo gold carbene that is attacked by a tethered arene to form a gold enolate, further reacting with a second quinoline N -oxide to complete the olefination process.