170489-16-4Relevant articles and documents
Cobalt-Catalyzed Enantioselective C–H Arylation of Indoles
Ackermann, Lutz,Jacob, Nicolas,Oliveira, Jo?o C. A.,Wencel-Delord, Joanna,Zaid, Yassir
supporting information, p. 798 - 806 (2022/02/03)
Atropoisomeric (hetero)biaryls are scaffolds with increasing importance in the pharmaceutical and agrochemical industries. Although it is the most obvious disconnection to construct such compounds, the direct enantioselective C–H arylation through the concomitant induction of the chiral information remains extremely challenging and uncommon. Herein, the unprecedented earth-abundant 3d-metal-catalyzed atroposelective direct arylation is reported, furnishing rare atropoisomeric C2-arylated indoles. Kinetic studies and DFT computation revealed an uncommon mechanism for this asymmetric transformation, with the oxidative addition being the rate- and enantio-determining step. Excellent stereoselectivities were reached (up to 96% ee), while using an unusual N-heterocyclic carbene ligand bearing an essential remote substituent. Attractive dispersion interactions along with positive C–H-π interactions exerted by the ligand were identified as key factors to guarantee the excellent enantioselection.
Electrochemically Enabled C3-Formylation and -Acylation of Indoles with Aldehydes
Yang, Liquan,Liu, Zhaoran,Li, Yujun,Lei, Ning,Shen, Yanling,Zheng, Ke
supporting information, p. 7702 - 7707 (2019/10/19)
Reported herein is an effective strategy for oxidative cross-coupling of indoles with various aldehydes. The strategy is based on a two-step transformation via a well-known Mannich-type reaction and a C-N bond cleavage for carbonyl introduction. The key step - the C-N bond cleavage of the Mannich product - was enabled by electrochemistry. This strategy (with over 40 examples) ensures excellent functional-group tolerance as well as late-stage functionalization of pharmaceutical molecules.
Method for performing formylation reaction of indole compound by photocatalysis of carbazolyl-conjugated micro-porous polymers (CMPs)
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Paragraph 0035-0040, (2018/07/30)
The invention discloses a method for performing formylation reaction of an indole compound by photocatalysis of carbazolyl-conjugated micro-porous polymers (CMPs). The method is characterized in thatin an oxygen-containing atmosphere and water/organic mixed solvent system, the indole compound and a methylamine compound are subjected to formylation reaction under the catalytic action of iodized salt and CMPs and illumination conditions so as to obtain a 3-formaldehyde indole compound. The method has mild reaction conditions, can be implemented under room temperature and illumination conditionsand can be used for obtaining the target product in high selectivity and high yield, the reaction belongs to heterogeneous catalysis reaction, the catalyst can be recovered and recycled, and industrial production is facilitated.