《Mechanistic insights into Cu-catalyzed enantioselective Friedel-Crafts reaction between indoles and 2-aryl-N-sulfonylaziridines》 was written by Wang, Ping; Zhao, Yang; Chapagain, Biplav; Yang, Yonggang; Liu, Wei; Wang, Yong. Product Details of 210169-54-3 And the article was included in Catalysis Science & Technology in 2020. The article conveys some information:
Computational studies were successfully carried out to provide mechanistic insights into LCu-catalyzed (L = (S)-Segphos ligand) Friedel-Crafts (F-C) reaction between indoles and 2-aryl-N-sulfonylaziridines. The proposed enantioselective mechanistic roles for the LCu-catalyzed F-C reaction were carefully considered: C-N bond cleavage through a three-membered ring transition state, C-C bond formation, oxidative addition, and reductive elimination. Through the energy decomposition anal. (EDA) on all possible transition states of the rate-determining step (RDS), the smaller ΔEdef(total) and the larger ΔEint were found in TS3R, resulting in the lowest activation energy (ΔE#). In other words, TS3R was the most kinetically favorable with the lowest activation barrier. Afterwards, the noncovalent interactions (C-H···π and π···π) and the steric effects were identified as playing a pivotal role in a favorable transition state for the C-C bond formation. In addition, the frontier MO (FMO) revealed that the smallest energy gap (5.2836 eV) between the highest occupied orbital (HOMO) and the lowest unoccupied orbital (LUMO) was found in TS3R.(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Product Details of 210169-54-3) was used in this study.
(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3) may be used for: regio- and stereoselective preparation of axially chiral arylnaphthalene derivatives via rhodium-catalyzed [2+2+2] cycloaddition of diynes with naphthalenepropynoic acid derivatives or diastereo- and enantioselective hydrogenation of α-amino-β-keto ester hydrochlorides catalyzed by an iridium complex.Product Details of 210169-54-3
Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis