title: Copper-mediated intramolecular oxidative C-H/C-H cross-coupling of α-oxo ketene N,S-acetals for indole synthesis.
abstract: CuCl2-mediated intramolecular C-H/C-H cross-dehydrogenative coupling (CDC) of thioalkyl-substituted α-acetyl or α-aroyl ketene N,S-acetals afforded 2-thioalkyl indoles. Tunable C-S bond transformations of the resultant indoles led to highly functionalized N-heterocyclic compounds. A β-thioalkyl is necessary to activate the N,S-acetal substrate and enable the CDC reaction to occur, and the relevant mechanism studies revealed that the CDC reaction follows a radical pathway.
authors.affiliation: Dalian Institute of Chemical Physics, Chinese Academy of Sciences , 457 Zhongshan Road, Dalian 116023, People's Republic of China.
authors.forename: Fei
authors.initials: F
authors.lastname: Huang
authors.forename: Ping
authors.initials: P
authors.lastname: Wu
authors.forename: Liandi
authors.initials: L
authors.lastname: Wang
authors.forename: Jiping
authors.initials: J
authors.lastname: Chen
authors.forename: Chenglin
authors.initials: C
authors.lastname: Sun
authors.forename: Zhengkun
authors.initials: Z
authors.lastname: Yu
mesh_terms: D000080:Acetals / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D005030:Ethylenes / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000080:Acetals; D005030:Ethylenes; D007211:Indoles; D007659:Ketones; D003300:Copper; C008223:ketene