1219637-79-2Relevant academic research and scientific papers
Iridium-catalyzed C-H borylation-based synthesis of natural indolequinones
Wang, Christy,Sperry, Jonathan
, p. 2584 - 2587 (2012)
An iridium-catalyzed C-H borylation provides the key step in a short synthesis of two indolequinone natural products. This regioselective C-H functionalization strategy delivers 7-borylindoles that undergo facile oxidation-hydrolysis to 7-hydroxyindoles and subsequent oxidation to the desired indolequinones, thereby demonstrating a powerful application of the iridium-catalyzed C-H borylation reaction. A significant result has arisen from the iridium-catalyzed borylation of N-diethylhydrosilyl-6-methoxyindole; even in the presence of a substituent at C6, the N-hydrosilyl group still directs borylation exclusively into the more sterically hindered C7 position in preference to C2.
Convergent total syntheses of the amaryllidaceae alkaloids lycoranine A, lycoranine B, and 2-methoxypratosine
Kim, Hye Sun,Banwell, Martin G.,Willis, Anthony C.
, p. 5103 - 5109 (2013/07/05)
The title alkaloids, 1, 2, and 3 respectively, have been prepared in a convergent manner by two related routes. The superior one involves C-H functionalization of the relevant 5-methoxyindole at C-7 using Hartwig's protocol and thus forming the correspond
Iridium-catalyzed, silyl-directed borylation of nitrogen-containing heterocycles
Robbins, Daniel W.,Boebel, Timothy A.,Hartwig, John F.
supporting information; experimental part, p. 4068 - 4069 (2010/05/01)
Chemical Figure Presented Selective methods for the functionalization of indoles and other nitrogen heterocycles would provide access to the core structures of many natural products and pharmaceuticals. Although there are many methods and strategies for the synthesis of substituted indoles or functionalization of the azole ring, strategies for the selective functionalization of the benzo-fused portion of the indole skeleton, particularly the 7-position, are less common. We report a one-pot, iridium-catalyzed, silyl-directed C-H borylation of indoles at the 7-position. This process occurs in high yield with a variety of substituted indoles, and conversions of the 7-borylindole products to 7-aryl-, 7-cinnamyl-, and 7-haloindoles are demonstrated. The lr-catalyzed, silyl-directed C-H borylation also occurs with several other nitrogen heterocycles, including carbazole, phenothiazines, and tetrahydroquinoline. The utility of this methodology is highlighted by the one-pot synthesis of a member of the pyrrolophenanthrldone class of alkaloid natural products. Copyright
