Quaternary Centers by Nickel‐Catalyzed Cross‐Coupling of Tertiary Carboxylic Acids and (Hetero)Aryl Zinc Reagents

This work bridges a gap in the cross‐coupling of aliphatic redox‐active esters with aryl zinc reagents. Previously limited to primary, secondary, and specialized tertiary centers, a new protocol has been devised to enable the coupling of general tertiary systems using nickel catalysis. The scope of...

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Bibliographic Details
Published in:Angewandte Chemie 2019-02, Vol.131 (8), p.2476-2480
Main Authors: Chen, Tie‐Gen, Zhang, Haolin, Mykhailiuk, Pavel K., Merchant, Rohan R., Smith, Courtney A., Qin, Tian, Baran, Phil S.
Format: Article
Language:English
Subjects:
Aliphatic compounds
Aromatic compounds
Carboxylic acids
Catalysis
Chemistry
Coupling
Decarboxylierende Radikalkupplungen
Esters
Nickel
Nickel-Katalyse
Quartäre Zentren
Reagents
Redoxaktive Ester
Tertiäre Säuren
Zinc
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Summary:This work bridges a gap in the cross‐coupling of aliphatic redox‐active esters with aryl zinc reagents. Previously limited to primary, secondary, and specialized tertiary centers, a new protocol has been devised to enable the coupling of general tertiary systems using nickel catalysis. The scope of this operationally simple method is broad, and it can be used to simplify the synthesis of medicinally relevant motifs bearing quaternary centers. Austausch am quartären Zentrum: Vollständig substituierte Kohlenstoffzentren mit einem Carboxylat‐Substituenten reagieren in Nickel‐katalysierten decarboxylierenden Kreuzkupplungen mit Arylzinkreagentien.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201814524