Copper-Catalyzed Cascade Cyclization of Indolyl Homopropargyl Amides: Stereospecific Construction of Bridged Aza-[n.2.1] Skeletons was written by Tan, Tong-De;Zhu, Xin-Qi;Bu, Hao-Zhen;Deng, Guocheng;Chen, Yang-Bo;Liu, Rai-Shung;Ye, Long-Wu. And the article was included in Angewandte Chemie, International Edition in 2019.SDS of cas: 349404-93-9 The following contents are mentioned in the article:
Catalytic cycloisomerization-initiated cascade cyclizations of terminal alkynes have received tremendous interest, and been widely used in the facile synthesis of a diverse array of valuable complex heterocycles. However, these tandem reactions have been mostly limited to noble-metal catalysis, and are initiated by an exo-cyclization pathway. Reported herein is an unprecedented copper-catalyzed endo-cyclization-initiated tandem reaction of indolyl homopropargyl amides, where copper catalyzes both the hydroamination and Friedel-Crafts alkylation process [e.g., I → II (85%)]. This method allows the practical and atom-economical synthesis of valuable bridged aza-[n.2.1] skeletons (n=3-6) with wide substrate scope, and excellent diastereoselectivity and enantioselectivity by a chirality-transfer strategy. Moreover, the mechanistic rationale for this novel cascade cyclization is also strongly supported by control experiments, and is distinctively different from the related gold catalysis. This study involved multiple reactions and reactants, such as 4-Bromo-N-(2-iodophenyl)benzenesulfonamide (cas: 349404-93-9SDS of cas: 349404-93-9).
4-Bromo-N-(2-iodophenyl)benzenesulfonamide (cas: 349404-93-9) belongs to iodide derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.SDS of cas: 349404-93-9
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com