Iron(III) catalyzed halo-functionalization of alkynes. Issue 27 (1st July 2015)

• Record Type: Journal Article
• Authors: Catano, Bryant; Lee, John; Kim, Claudia; Farrell, David; Petersen, Jeffrey L.; Xing, Yalan
• Is Part Of: Tetrahedron letters. Volume 56:Issue 27(2015)
• Page Start: 4124
• Page End: 4127
• Publication Date: 2015-07-01
• Subjects: Alkyne -- Halo-functionalization -- One-pot -- Iron; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.05.039
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: Aromatic and aliphatic alkynes can be halo-functionalized to α, α-dihalodimethyl ketals catalyzed by FeCl3 in excellent yields. MeOH is used as a nucleophilic solvent and N -halosuccinimide as the halogen source for this efficient transformation. The resulting α, α-dibromodimethyl ketals can be converted to the corresponding α, α-dibromoketones by treatment with 8% FeCl3 in silica gel.