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Preparation of Functionalized Diaryl‐ and Diheteroaryllanthanum Reagents by Fast Halogen–Lanthanum Exchange
Author(s) -
Benischke Andreas D.,
AnthoreDalion Lucile,
Berionni Guillaume,
Knochel Paul
Publication year - 2017
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.201709553
Subject(s) - electrophile , halogen , lanthanum , chemistry , reagent , halide , aryl , reactivity (psychology) , medicinal chemistry , organic chemistry , combinatorial chemistry , catalysis , alkyl , medicine , alternative medicine , pathology
Aryl and heteroaryl halides (X=Br, I) undergo a fast and convenient halogen–lanthanum exchange with nBu 2 LaMe, which leads to functionalized diaryl‐ and diheteroaryllanthanum derivatives. Subsequent trapping reactions with selected electrophiles, such as ketones, aldehydes, or amides, proceeded smoothly at −50 °C in THF, affording polyfunctionalized alcohols and carbonyl derivatives. Kinetic competition experiments revealed a similar reactivity trend as for Br/Mg exchange, but 10 6 ‐times higher rates, making it comparable to Br/Li exchange.