title: Brønsted Acid Catalyzed Oxygenative Bimolecular Friedel-Crafts-type Coupling of Ynamides.
abstract: A non-metal approach for accessing α-oxo carbene surrogates for a C-C bond-forming bimolecular coupling between ynamides and nucleophilic arenes was developed. This acid-catalyzed coupling features mild temperature, which is critical for the required temporal chemoselectivity among nucleophiles. The scope of nucleophiles includes indoles, pyrroles, anilines, phenols and silyl enolethers. Furthermore, a direct test of SN2' mechanism has been provided by employing chiral N,N'-dioxides which also enlightens the nature of the intermediates in related metal-catalyzed processes.
authors.affiliation: Department of Chemistry & Center for New Directions in Organic Synthesis (CNOS), Hanyang University, 222 Wangsimni-ro, Seong-gu, Seoul, 04763, Korea.
authors.forename: Dilip V
authors.initials: DV
authors.lastname: Patil
authors.affiliation: Department of Chemistry & Center for New Directions in Organic Synthesis (CNOS), Hanyang University, 222 Wangsimni-ro, Seong-gu, Seoul, 04763, Korea.
authors.forename: Seung Woo
authors.initials: SW
authors.lastname: Kim
authors.affiliation: Department of Chemistry & Center for New Directions in Organic Synthesis (CNOS), Hanyang University, 222 Wangsimni-ro, Seong-gu, Seoul, 04763, Korea.
authors.forename: Quynh H
authors.initials: QH
authors.lastname: Nguyen
authors.affiliation: Department of Chemistry & Center for New Directions in Organic Synthesis (CNOS), Hanyang University, 222 Wangsimni-ro, Seong-gu, Seoul, 04763, Korea.
authors.forename: Hanbyul
authors.initials: H
authors.lastname: Kim
authors.affiliation: Department of Chemistry & Center for New Directions in Organic Synthesis (CNOS), Hanyang University, 222 Wangsimni-ro, Seong-gu, Seoul, 04763, Korea.
authors.forename: Shan
authors.initials: S
authors.lastname: Wang
authors.affiliation: Department of Chemistry & Center for New Directions in Organic Synthesis (CNOS), Hanyang University, 222 Wangsimni-ro, Seong-gu, Seoul, 04763, Korea.
authors.forename: Tuan
authors.initials: T
authors.lastname: Hoang
authors.affiliation: Department of Chemistry & Center for New Directions in Organic Synthesis (CNOS), Hanyang University, 222 Wangsimni-ro, Seong-gu, Seoul, 04763, Korea.
authors.forename: Seunghoon
authors.identifier: 0000-0003-1702-8918
authors.initials: S
authors.lastname: Shin
keywords: Brønsted acid catalysis; intermolecular trapping; pyridine-N-oxides; ynamides; α-oxo carbene surrogate