Recent Advances in the I₂-Catalyzed C-H Bond Functionalizations

Abstract

Strem Chemicals, Inc., established in 1964, is a privately held manufacturer & marketer of high purity specialty chemicals. Strem's products are used for R&D and commercial scale applications, especially in the pharmaceutical, microelectronics, chemicals & petrochemicals industries. Some key products include catalysts, ligands, organometallics, CVD/ALD precursors and nanomaterials. For more information, N N Cu CF 3

One-Pot Synthesis of Furo[3,4-c]indolo[2,1-a]isoquinolines through Rh(III)-Catalyzed Cascade Reactions of 2-Phenylindoles with 4-Hydroxy-2-alkynoates

“…4-Hydroxy-2-alkynoates, containing ester and hydroxyl groups, could further undergo lactonization through ester exchange after alkynyl insertion . Within the context of our ongoing efforts to build heterocycles and perform clean C–H bond functionalization, we herein disclose the synthesis of indole-containing pentacycles through Rh-catalyzed cascade reactions of 2-phenylindoles with 4-hydroxy-2-alkynoates. This reaction exhibits high efficiency and regioselectivity and tolerates various functional groups.…”

Metal‐Free, Visible‐Light Promoted Intramolecular Azole C−H Bond Amination Using Catalytic Amount of I2: A Route to 1,2,3‐Triazolo[1,5‐a]quinazolin‐5(4H)‐ones

“…To our delight, the desired C−H bond amination product 2 a was obtained in 11% or 72% yield respectively when 2 equivalents of PhI(OCOCF 3 ) 2 or PhI(OAc) 2 were used, and PhI(OAc) 2 was the optimal oxidant (Table 1, entries 2 and 3). The use of NaI or TBAI instead of elementary I 2 as the catalyst was also suitable for the reaction, albeit with only moderate yields (Table 1, entries 7 and 8) [10a,14] . Shortening the reaction time have a significant effect on the yield (Table 1, entries 9–11), and the desired product 2 a was obtained in a highest yield of 93% over 4 hours (with 90% isolated yield).…”

Tandem Construction of Indole-Fused Phthalazines from (2-Alkynylbenzylidene)hydrazines under Metal-Free Conditions

“…On the other hand, the participation of transition metals in these protocols limited their further applications in the pharmaceutical industry . Continuing our studies on versatile heterocyclic constructions, we herein disclose the first successful constructions of a series of indole-fused phthalazines through radical process, which comprise the versatile pyrrolo­[2,1- b ]­phthalazine core (Scheme B). The key point of this transformation is from an unexpected selective 6- exo-dig cycloaddition of (2-alkynylbenzylidene)­hydrazines under air atmosphere.…”