Ir-catalyzed C–H silylations of phenyldeazapurines. Issue 49 (9th December 2015)

• Record Type: Journal Article
• Authors: Sabat, Nazarii; Poštová Slavětínská, Lenka; Hocek, Michal
• Is Part Of: Tetrahedron letters. Volume 56:Issue 49(2015)
• Page Start: 6860
• Page End: 6862
• Publication Date: 2015-12-09
• Subjects: C–H silylation -- Deazapurines -- Iridium catalysis -- C–H activations; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.10.089
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: A study of the Ir-catalyzed C–H silylation of 6-phenyl-7-deazapurines or -9-deazapurines with trialkylsilanes revealed that this reaction preferentially proceeded via ortho -silylation at the aryl group due to the directing effect of the N1 nitrogen of the deazapurine, rather than C–H silylation at the heterocycle which was only a minor side-reaction. A preparative protocol for the ortho -silylation of aryldeazapurines is presented.