Gold(I)-Catalyzed Synthesis of 2,2'-Biindoles via One-Pot Double Cycloisomerization Strategy
Jaime G Ibarra-Gutiérrez1, César R Solorio-Alvarado1, Luis Chacón-García2
1Campus Guanajuato, División de Ciencias Naturales y Exactas, Departamento de Química, Universidad de Guanajuato, Noria Alta S/N, 36050 Guanajuato, Guanajuato, México.
Abstract:
The first systematic, concise and target-directed gold(I)-catalyzed synthesis of a family of 2,2'-biindoles containing different substitution patterns is described. The developed protocol involves the synthesis of 1,3-diyne-anilines followed by a one-pot gold(I)-catalyzed double cycloisomerization, giving rise to an efficient, broad and general protocol to get different 2,2'-biindoles under mild reaction conditions. Due to the methodological restriction of present methods for accessing this class of compounds, herein we present our synthetic proposal which allowed the preparation of several examples of 2,2'-biindoles. Their functionalization-guided us to the discovery that the chemical stability, is substitution structure-dependent.
More Related Videos
07:36Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Related Concept Videos
Cycloaddition Reactions: Overview
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
