title: Pd(0)-Catalyzed Dearomative Diarylation of Indoles.
abstract: We have developed a protocol for a Pd(0)-catalyzed dearomative syn 1,2-diarylation of indoles using readily available boroxines (dehydrated boronic acids) as coupling partners. This reaction proceeds efficiently using PtBu3 as the ligand to divergently access to fused indolines while minimizing the extent of direct Suzuki coupling. The scope of the reaction is remarkably broad and all products are obtained as single diastereomers in moderate to excellent yields. We have also compiled data which parallels the steric and electronic properties of both substrate and boroxine with the propensity to undergo the desired dearomative process over direct Suzuki coupling.
authors.affiliation: Department of Chemistry, University of Toronto, 80 St. George St., Toronto, M5S 3H6, Canada.
authors.forename: David A
authors.initials: DA
authors.lastname: Petrone
authors.affiliation: Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, 466-8555, Japan.
authors.forename: Masaru
authors.initials: M
authors.lastname: Kondo
authors.affiliation: Department of Chemistry, University of Toronto, 80 St. George St., Toronto, M5S 3H6, Canada.
authors.forename: Nicolas
authors.initials: N
authors.lastname: Zeidan
authors.affiliation: Department of Chemistry, University of Toronto, 80 St. George St., Toronto, M5S 3H6, Canada. mlautens@chem.utoronto.ca.
authors.forename: Mark
authors.identifier: http://orcid.org/0000-0002-0179-2914
authors.initials: M
authors.lastname: Lautens
keywords: C−C coupling; diastereoselectivity; heterocycles; homogeneous catalysis; palladium