title: Catalyst-controlled chemoselective reaction of 3-indolylmethanols with cyclic enaminones leading to C2-functionalized indoles.
abstract: A catalyst-controlled chemoselective formal 1,2-addition of 3-indolylmethanols with cyclic enaminones has been established in the presence of TfOH as a strong acid, which afforded C2-functionalized indole derivatives in generally good yields (up to 89% yield). This reaction not only confronted the great challenge in 1,2-addition of 3-indolylmethanols but also provided a good strategy for C2-functionalization of indole derivatives. The investigation on the reaction mechanism revealed that this formal 1,2-addition included a tandem sequence of 1,4-addition/[1,3]-C migration/isomerization, in which the [1,3]-C migration of the 1,4-addition product was a key step and the acidity of the catalyst played a decisive role in the observed chemoselectivity.
authors.affiliation: School of Chemistry & Chemical Engineering, and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University , Xuzhou, 221116, China.
authors.forename: Xin
authors.initials: X
authors.lastname: Li
authors.forename: Wei
authors.initials: W
authors.lastname: Tan
authors.forename: Yu-Xin
authors.initials: YX
authors.lastname: Gong
authors.forename: Feng
authors.initials: F
authors.lastname: Shi
mesh_terms: D002384:Catalysis; D003500:Cyclization; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D007211:Indoles