863870-43-3Relevant academic research and scientific papers
A highly selective tandem cross-coupling of gem-dihaloolefins for a modular, efficient synthesis of highly functionalized indoles
Fang, Yuan-Qing,Lautens, Mark
, p. 538 - 549 (2008/09/17)
(Chemical Equation Presented) A highly efficient method of indole synthesis using gem-dihalovinylaniline substrates and an organoboron reagent was developed via a Pd-catalyzed tandem intramolecular amination and an intermolecular Suzuki coupling. Aryl, alkenyl, and alkyl boron reagents are all successfully employed, making for a versatile modular approach. The reaction tolerates a variety of substitution patterns on the aniline leading to indoles with group at C2-C7. The orthogonal approach of the sequential copper- and palladium-mediated synthesis of 1,2-diarylindoles exploited the wide availability of diverse organoboron reagents.
Cul-catalyzed tandem intramolecular amidation using gem-dibromovinyl systems
Yuen, Josephine,Fang, Yuan-Qing,Lautens, Mark
, p. 653 - 656 (2007/10/03)
Imidazoindolones are present as the key structural motif in the family of antifungals, fumiquinazolines, and the antagonist asperlicin. The first example of a Cul-catalyzed tandem intramolecular amidation forming substituted imidazoindolones from readily
Pd-catalyzed tandem C-N/C-C coupling of gem-dihalovinyl systems: A modular synthesis of 2-substituted indoles
Fang, Yuan-Qing,Lautens, Mark
, p. 3549 - 3552 (2007/10/03)
(Chemical Equation Presented) 2-Substituted indoles were synthesized via a Pd-catalyzed tandem C-N/Suzuki-Miyaura coupling from readily prepared ortho-gem-dihalovinylanilines. Optimal conditions used a Pd(OAc) 2/S-Phos catalyst in the presence of K3PO 4·H2O and an organoboron reagent, which included boronic acids, esters, alkyl 9-BBN derivatives, and trialkylboranes. Yields of the desired indoles were good to excellent using low catalyst loadings (typically 1 mol %).
