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Synthesis of Nitrile‐Bearing Quaternary Centers by an Equilibrium‐Driven Transnitrilation and Anion‐Relay Strategy
Author(s) -
Alazet Sébastien,
West Michael S.,
Patel Purvish,
Rousseaux Sophie A. L.
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201903215
Subject(s) - nitrile , electrophile , chemistry , reagent , lithium (medication) , combinatorial chemistry , alkyl , ion , bearing (navigation) , relay , organic chemistry , computer science , catalysis , physics , power (physics) , quantum mechanics , artificial intelligence , endocrinology , medicine
The efficient preparation of nitrile‐containing building blocks is of interest due to their utility as synthetic intermediates and their prevalence in pharmaceuticals. As a result, significant efforts have been made to develop methods to access these motifs which rely on safer and non‐toxic sources of CN. Herein, we report that 2‐methyl‐2‐phenylpropanenitrile is an efficient, non‐toxic, electrophilic CN source for the synthesis of nitrile‐bearing quaternary centers by a thermodynamic transnitrilation and anion‐relay strategy. This one‐pot process leads to nitrile products resulting from the gem ‐difunctionalization of alkyl lithium reagents.