Rh(III)-Catalyzed Asymmetric Synthesis of Axially Chiral Biindolyls by Merging C–H Activation and Nucleophilic Cyclization
Journal of the American Chemical Society2019Vol. 141(24), pp. 9527–9532
Citations Over TimeTop 1% of 2019 papers
Abstract
Enantiomeric access to pentatomic biaryls is challenging due to their relatively low rotational barrier. Reported herein is the mild and highly enantioselective synthesis of 2,3'-biindolyls via underexplored integration of C-H activation and alkyne cyclization using a unified chiral Rh(III) catalyst. The reaction proceeded via initial C-H activation followed by alkyne cyclization. A chiral rhodacyclic intermediate has been isolated from stoichiometric C-H activation, which offers direct mechanistic insight.
Related Papers
- → Hydrotris(3-mesitylpyrazolyl)borato-copper(i) alkyne complexes: synthesis, structural characterization and rationalization of their activities as alkyne cyclopropenation catalysts(2012)25 cited
- → Strong coordination of cycloheptynes by gold(i) chloride: synthesis and structure of two complexes of the type [(alkyne)AuCl](1998)58 cited
- → Studies on the Chemical Transformations of Simple Condensates Derived from 3-Formylchromone under Nucleophilic Conditions(2013)17 cited
- → Nucleophilic Additions to Alkynes and Reactions via Vinylidene Intermediates(2004)19 cited
- → Protection for the Alkyne CH(2014)2 cited